DE2215409C3 - Halogen-nitro-2,2'methylendiphenole, ihre Salze und Ester, Verfahren zu ihrer Herstellung und ihre Verwendung - Google Patents
Halogen-nitro-2,2'methylendiphenole, ihre Salze und Ester, Verfahren zu ihrer Herstellung und ihre VerwendungInfo
- Publication number
- DE2215409C3 DE2215409C3 DE2215409A DE2215409A DE2215409C3 DE 2215409 C3 DE2215409 C3 DE 2215409C3 DE 2215409 A DE2215409 A DE 2215409A DE 2215409 A DE2215409 A DE 2215409A DE 2215409 C3 DE2215409 C3 DE 2215409C3
- Authority
- DE
- Germany
- Prior art keywords
- nitro
- methylenediphenol
- yield
- theory
- mixture
- 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
Links
- 150000003839 salts Chemical class 0.000 title claims description 5
- 150000002148 esters Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title description 10
- 238000002360 preparation method Methods 0.000 title description 7
- 230000008569 process Effects 0.000 title description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 title 1
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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 group [H]* 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 description 81
- 150000001875 compounds Chemical class 0.000 description 58
- 239000000203 mixture Substances 0.000 description 42
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 40
- 239000000243 solution Substances 0.000 description 40
- 238000000746 purification Methods 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 229960000583 acetic acid Drugs 0.000 description 20
- 239000012362 glacial acetic acid Substances 0.000 description 20
- 238000010626 work up procedure Methods 0.000 description 17
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
- 238000000354 decomposition reaction Methods 0.000 description 12
- 208000006275 fascioliasis Diseases 0.000 description 12
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- -1 acyloxy radical Chemical class 0.000 description 9
- 244000045947 parasite Species 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 241000242711 Fasciola hepatica Species 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 235000013601 eggs Nutrition 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
- 241001494479 Pecora Species 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- MQCPOLNSJCWPGT-UHFFFAOYSA-N 2,2'-Bisphenol F Chemical class OC1=CC=CC=C1CC1=CC=CC=C1O MQCPOLNSJCWPGT-UHFFFAOYSA-N 0.000 description 6
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- YRRUNVSYSHQUNN-UHFFFAOYSA-N 4-chloro-2-[(5-chloro-2-hydroxyphenyl)methyl]-6-nitrophenol Chemical compound ClC1=CC(=C(C(=C1)[N+](=O)[O-])O)CC1=C(C=CC(=C1)Cl)O YRRUNVSYSHQUNN-UHFFFAOYSA-N 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 239000011592 zinc chloride Substances 0.000 description 5
- 235000005074 zinc chloride Nutrition 0.000 description 5
- OUQDXGWUMIPVGE-UHFFFAOYSA-N 2-[(5-bromo-2-hydroxyphenyl)methyl]-4,6-dinitrophenol Chemical compound BrC1=CC(=C(C=C1)O)CC1=C(C(=CC(=C1)[N+](=O)[O-])[N+](=O)[O-])O OUQDXGWUMIPVGE-UHFFFAOYSA-N 0.000 description 4
- BBOJDJDFWQFYSM-UHFFFAOYSA-N 2-[(5-chloro-2-hydroxy-3-nitrophenyl)methyl]-6-iodo-4-nitrophenol Chemical compound ClC1=CC(=C(C(=C1)[N+](=O)[O-])O)CC1=C(C(=CC(=C1)[N+](=O)[O-])I)O BBOJDJDFWQFYSM-UHFFFAOYSA-N 0.000 description 4
- WHFVOSYRFPSIQJ-UHFFFAOYSA-N 3,4,6-trichloro-2-[(2-hydroxy-5-nitrophenyl)methyl]phenol Chemical compound ClC=1C(=C(C(=CC1Cl)Cl)O)CC1=C(C=CC(=C1)[N+](=O)[O-])O WHFVOSYRFPSIQJ-UHFFFAOYSA-N 0.000 description 4
- RHWDEIXKHGCDOG-UHFFFAOYSA-N 4-iodo-2-nitrophenol Chemical compound OC1=CC=C(I)C=C1[N+]([O-])=O RHWDEIXKHGCDOG-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 210000003608 fece Anatomy 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical class OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- RAXQGPNKSYGAAN-UHFFFAOYSA-N 2-[(3-bromo-5-chloro-2-hydroxyphenyl)methyl]-4-chloro-6-nitrophenol Chemical compound BrC1=CC(=CC(=C1O)CC1=C(C(=CC(=C1)Cl)[N+](=O)[O-])O)Cl RAXQGPNKSYGAAN-UHFFFAOYSA-N 0.000 description 3
- RGGVDCHSGWFJMH-UHFFFAOYSA-N 2-bromo-6-[(5-bromo-2-hydroxy-3-nitrophenyl)methyl]-4-nitrophenol Chemical compound BrC1=CC(=C(C(=C1)[N+](=O)[O-])O)CC1=C(C(=CC(=C1)[N+](=O)[O-])Br)O RGGVDCHSGWFJMH-UHFFFAOYSA-N 0.000 description 3
- JYAZFYSJXBUATE-UHFFFAOYSA-N 2-bromo-6-[(5-fluoro-2-hydroxy-3-nitrophenyl)methyl]-4-nitrophenol Chemical compound OC1=C(Br)C=C([N+]([O-])=O)C=C1CC1=CC(F)=CC([N+]([O-])=O)=C1O JYAZFYSJXBUATE-UHFFFAOYSA-N 0.000 description 3
- ROCULTHJMHZLCO-UHFFFAOYSA-N 2-chloro-6-[(2-hydroxy-5-iodo-3-nitrophenyl)methyl]-4-nitrophenol Chemical compound ClC1=CC(=CC(=C1O)CC1=C(C(=CC(=C1)I)[N+](=O)[O-])O)[N+](=O)[O-] ROCULTHJMHZLCO-UHFFFAOYSA-N 0.000 description 3
- UBUPKXVSIJCJPV-UHFFFAOYSA-N 3,4,6-trichloro-2-[(2-hydroxy-3-iodo-5-nitrophenyl)methyl]phenol Chemical compound ClC=1C(=C(C(=CC1Cl)Cl)O)CC1=C(C(=CC(=C1)[N+](=O)[O-])I)O UBUPKXVSIJCJPV-UHFFFAOYSA-N 0.000 description 3
- ZGTJRQUHBWXFKT-UHFFFAOYSA-N 4-chloro-2-[(3,5-dibromo-2-hydroxyphenyl)methyl]-6-nitrophenol Chemical compound BrC1=CC(=C(C(=C1)Br)O)CC1=C(C(=CC(=C1)Cl)[N+](=O)[O-])O ZGTJRQUHBWXFKT-UHFFFAOYSA-N 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 208000025011 Distomatosis Diseases 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 229940126601 medicinal product Drugs 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- IKXCHOUDIPZROZ-LXGUWJNJSA-N (2r,3r,4r,5s)-6-(ethylamino)hexane-1,2,3,4,5-pentol Chemical compound CCNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO IKXCHOUDIPZROZ-LXGUWJNJSA-N 0.000 description 2
- JEIYIXDNZKATLC-UHFFFAOYSA-N 2-(hydroxymethyl)-4-nitrophenol Chemical compound OCC1=CC([N+]([O-])=O)=CC=C1O JEIYIXDNZKATLC-UHFFFAOYSA-N 0.000 description 2
- IUMORGKCPHMIBK-UHFFFAOYSA-N 2-[(3,5-dibromo-2-hydroxyphenyl)methyl]-4,6-dinitrophenol Chemical compound BrC1=CC(=C(C(=C1)Br)O)CC1=C(C(=CC(=C1)[N+](=O)[O-])[N+](=O)[O-])O IUMORGKCPHMIBK-UHFFFAOYSA-N 0.000 description 2
- RVNBSCYXURBPEP-UHFFFAOYSA-N 2-[(3-bromo-2-hydroxy-5-nitrophenyl)methyl]-3,4,6-trichlorophenol Chemical compound BrC1=CC(=CC(=C1O)CC1=C(C(=CC(=C1Cl)Cl)Cl)O)[N+](=O)[O-] RVNBSCYXURBPEP-UHFFFAOYSA-N 0.000 description 2
- LBZGPJJQBINRKH-UHFFFAOYSA-N 2-[(5-bromo-2-hydroxy-3-iodophenyl)methyl]-4,6-dinitrophenol Chemical compound BrC1=CC(=C(C(=C1)I)O)CC1=C(C(=CC(=C1)[N+](=O)[O-])[N+](=O)[O-])O LBZGPJJQBINRKH-UHFFFAOYSA-N 0.000 description 2
- ZBCPOYXCFINQFG-UHFFFAOYSA-N 2-[(5-bromo-2-hydroxy-3-nitrophenyl)methyl]-6-chloro-4-nitrophenol Chemical compound BrC1=CC(=C(C(=C1)[N+](=O)[O-])O)CC1=C(C(=CC(=C1)[N+](=O)[O-])Cl)O ZBCPOYXCFINQFG-UHFFFAOYSA-N 0.000 description 2
- UHDFSFQGOSTXPJ-UHFFFAOYSA-N 2-[(5-bromo-2-hydroxyphenyl)methyl]-4-chloro-6-nitrophenol Chemical compound BrC1=CC(=C(C=C1)O)CC1=C(C(=CC(=C1)Cl)[N+](=O)[O-])O UHDFSFQGOSTXPJ-UHFFFAOYSA-N 0.000 description 2
- VJGOYCJCDACINK-UHFFFAOYSA-N 3,4,6-tribromo-2-[(2-hydroxy-3-iodo-5-nitrophenyl)methyl]phenol Chemical compound BrC=1C(=C(C(=CC1Br)Br)O)CC1=C(C(=CC(=C1)[N+](=O)[O-])I)O VJGOYCJCDACINK-UHFFFAOYSA-N 0.000 description 2
- BOYCHYFKSISJDQ-UHFFFAOYSA-N 3,4,6-trichloro-2-[(3-chloro-2-hydroxy-5-nitrophenyl)methyl]phenol Chemical compound ClC=1C(=C(C(=CC1Cl)Cl)O)CC1=C(C(=CC(=C1)[N+](=O)[O-])Cl)O BOYCHYFKSISJDQ-UHFFFAOYSA-N 0.000 description 2
- CEFFUJIHZMPDID-UHFFFAOYSA-N 39224-65-2 Chemical compound OC1=CC(Cl)=C(Cl)C=C1[N+]([O-])=O CEFFUJIHZMPDID-UHFFFAOYSA-N 0.000 description 2
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 2
- UORLVGDPQPABCN-UHFFFAOYSA-N 4-chloro-2-[(3,5-dichloro-2-hydroxyphenyl)methyl]-6-nitrophenol Chemical compound ClC1=CC(=C(C(=C1)Cl)O)CC1=C(C(=CC(=C1)Cl)[N+](=O)[O-])O UORLVGDPQPABCN-UHFFFAOYSA-N 0.000 description 2
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 2
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 239000008101 lactose Substances 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
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 210000000813 small intestine Anatomy 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- XPUSKKJATQFMBF-UHFFFAOYSA-N 2,4,5-tribromophenol Chemical compound OC1=CC(Br)=C(Br)C=C1Br XPUSKKJATQFMBF-UHFFFAOYSA-N 0.000 description 1
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-Tribromophenol Natural products OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 1
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 description 1
- GZJHKJPMZZLHOC-UHFFFAOYSA-N 2-[(2-hydroxy-5-iodo-3-nitrophenyl)methyl]-6-iodo-4-nitrophenol Chemical compound IC1=CC(=C(C(=C1)[N+](=O)[O-])O)CC1=C(C(=CC(=C1)[N+](=O)[O-])I)O GZJHKJPMZZLHOC-UHFFFAOYSA-N 0.000 description 1
- KJRGBYZPXRZMMY-UHFFFAOYSA-N 2-[(2-hydroxyphenyl)methyl]-6-nitrophenol Chemical compound [N+](=O)([O-])C1=CC=CC(=C1O)CC1=C(C=CC=C1)O KJRGBYZPXRZMMY-UHFFFAOYSA-N 0.000 description 1
- RQNGHURPUZTTID-UHFFFAOYSA-N 2-[(3-bromo-5-chloro-2-hydroxyphenyl)methyl]-4,6-dinitrophenol Chemical compound BrC1=CC(=CC(=C1O)CC1=C(C(=CC(=C1)[N+](=O)[O-])[N+](=O)[O-])O)Cl RQNGHURPUZTTID-UHFFFAOYSA-N 0.000 description 1
- PMEOKKFPNASNSX-UHFFFAOYSA-N 2-[(5-bromo-2-hydroxy-3-nitrophenyl)methyl]-3,4,6-trichlorophenol Chemical compound BrC1=CC(=C(C(=C1)[N+](=O)[O-])O)CC1=C(C(=CC(=C1Cl)Cl)Cl)O PMEOKKFPNASNSX-UHFFFAOYSA-N 0.000 description 1
- YMJGSFXLJRZBPW-UHFFFAOYSA-N 2-[(5-bromo-2-hydroxy-3-nitrophenyl)methyl]-6-iodo-4-nitrophenol Chemical compound BrC1=CC(=C(C(=C1)[N+](=O)[O-])O)CC1=C(C(=CC(=C1)[N+](=O)[O-])I)O YMJGSFXLJRZBPW-UHFFFAOYSA-N 0.000 description 1
- LFCDDJWKDNCJEK-UHFFFAOYSA-N 2-[(5-bromo-2-hydroxyphenyl)methyl]-3,4,6-trichlorophenol Chemical compound BrC1=CC(=C(C=C1)O)CC1=C(C(=CC(=C1Cl)Cl)Cl)O LFCDDJWKDNCJEK-UHFFFAOYSA-N 0.000 description 1
- QPQNOMIIJGPILU-UHFFFAOYSA-N 2-[(5-chloro-2-hydroxy-3-nitrophenyl)methyl]-6-fluoro-4-nitrophenol Chemical compound ClC1=CC(=C(C(=C1)[N+](=O)[O-])O)CC1=C(C(=CC(=C1)[N+](=O)[O-])F)O QPQNOMIIJGPILU-UHFFFAOYSA-N 0.000 description 1
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- VSQUWQZIOUODSH-UHFFFAOYSA-N 2-bromo-6-[(2-hydroxy-5-iodo-3-nitrophenyl)methyl]-4-nitrophenol Chemical compound BrC1=CC(=CC(=C1O)CC1=C(C(=CC(=C1)I)[N+](=O)[O-])O)[N+](=O)[O-] VSQUWQZIOUODSH-UHFFFAOYSA-N 0.000 description 1
- PXZGZJASYGWQEQ-UHFFFAOYSA-N 2-bromo-6-[(5-fluoro-2-hydroxyphenyl)methyl]-4-nitrophenol Chemical compound BrC1=CC(=CC(=C1O)CC1=C(C=CC(=C1)F)O)[N+](=O)[O-] PXZGZJASYGWQEQ-UHFFFAOYSA-N 0.000 description 1
- DIRNVHCNISKNQF-UHFFFAOYSA-N 2-chloro-6-[(5-chloro-2-hydroxy-3-nitrophenyl)methyl]-4-nitrophenol Chemical compound OC1=C(Cl)C=C([N+]([O-])=O)C=C1CC1=CC(Cl)=CC([N+]([O-])=O)=C1O DIRNVHCNISKNQF-UHFFFAOYSA-N 0.000 description 1
- IODXLARDEPQBJC-UHFFFAOYSA-N 3,4,6-trichloro-2-[(2-hydroxy-5-iodo-3-nitrophenyl)methyl]phenol Chemical compound ClC=1C(=C(C(=CC1Cl)Cl)O)CC1=C(C(=CC(=C1)I)[N+](=O)[O-])O IODXLARDEPQBJC-UHFFFAOYSA-N 0.000 description 1
- CPESWRFORLFSBL-UHFFFAOYSA-N 3,4,6-trichloro-2-[(5-chloro-2-hydroxyphenyl)methyl]phenol Chemical compound ClC=1C(=C(C(=CC1Cl)Cl)O)CC1=C(C=CC(=C1)Cl)O CPESWRFORLFSBL-UHFFFAOYSA-N 0.000 description 1
- XUWRFFOZVUYNSZ-UHFFFAOYSA-N 3,4,6-trichloro-2-[(5-fluoro-2-hydroxy-3-nitrophenyl)methyl]phenol Chemical compound ClC=1C(=C(C(=CC1Cl)Cl)O)CC1=C(C(=CC(=C1)F)[N+](=O)[O-])O XUWRFFOZVUYNSZ-UHFFFAOYSA-N 0.000 description 1
- DSBOROFZRWWETA-UHFFFAOYSA-N 3,4-dichloro-2-[(2,3-dichloro-6-hydroxy-5-nitrophenyl)methyl]-6-nitrophenol Chemical compound C(C1=C(C(=CC(=C1Cl)Cl)[N+](=O)[O-])O)C1=C(C(=CC(=C1Cl)Cl)[N+](=O)[O-])O DSBOROFZRWWETA-UHFFFAOYSA-N 0.000 description 1
- CUTFAPGINUFNQM-UHFFFAOYSA-N 4-bromo-2-nitrophenol Chemical compound OC1=CC=C(Br)C=C1[N+]([O-])=O CUTFAPGINUFNQM-UHFFFAOYSA-N 0.000 description 1
- VGKHVVJRFPLSIP-UHFFFAOYSA-N 4-chloro-2-[(5-chloro-2-hydroxy-3-iodophenyl)methyl]-6-nitrophenol Chemical compound ClC1=CC(=C(C(=C1)I)O)CC1=C(C(=CC(=C1)Cl)[N+](=O)[O-])O VGKHVVJRFPLSIP-UHFFFAOYSA-N 0.000 description 1
- RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 1
- ORPHLVJBJOCHBR-UHFFFAOYSA-N 403-19-0 Chemical compound OC1=CC=C([N+]([O-])=O)C=C1F ORPHLVJBJOCHBR-UHFFFAOYSA-N 0.000 description 1
- BWQWBOCFVUBGEF-UHFFFAOYSA-N 5847-57-4 Chemical compound OC1=CC(Cl)=C([N+]([O-])=O)C=C1Cl BWQWBOCFVUBGEF-UHFFFAOYSA-N 0.000 description 1
- BOFRXDMCQRTGII-UHFFFAOYSA-N 619-08-9 Chemical compound OC1=CC=C([N+]([O-])=O)C=C1Cl BOFRXDMCQRTGII-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- MMYHZEDBTMXYAF-UHFFFAOYSA-N Bromofenofos Chemical compound OC1=C(Br)C=C(Br)C=C1C1=CC(Br)=CC(Br)=C1OP(O)(O)=O MMYHZEDBTMXYAF-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 108091028109 FinP Proteins 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- FCSHMCFRCYZTRQ-UHFFFAOYSA-N N,N'-diphenylthiourea Chemical compound C=1C=CC=CC=1NC(=S)NC1=CC=CC=C1 FCSHMCFRCYZTRQ-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 101000971427 Plasmodium falciparum Knob-associated histidine-rich protein Proteins 0.000 description 1
- 241000242680 Schistosoma mansoni Species 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 210000000683 abdominal cavity Anatomy 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 230000002141 anti-parasite Effects 0.000 description 1
- 230000000347 anti-schistosomal effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical class C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 210000003445 biliary tract Anatomy 0.000 description 1
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 1
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000007265 chloromethylation reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- UNNFUOQPVNQPFU-UHFFFAOYSA-N n-phenyl-2-sulfanylbenzamide Chemical compound SC1=CC=CC=C1C(=O)NC1=CC=CC=C1 UNNFUOQPVNQPFU-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
- JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 description 1
- 239000001230 potassium iodate Substances 0.000 description 1
- 235000006666 potassium iodate Nutrition 0.000 description 1
- 229940093930 potassium iodate Drugs 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical class OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 description 1
- 229950000975 salicylanilide Drugs 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 238000003307 slaughter Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/26—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups and being further substituted by halogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7104839.A NL167151C (nl) | 1971-04-09 | 1971-04-09 | Werkwijze ter bereiding van geneesmiddelen met anti-parasitaire werking op basis van halogeen bevatten- de 2,2'-methyleendifenolderivaten, alsmede werkwijze ter bereiding van deze geneeskrachtige verbindingen. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2215409A1 DE2215409A1 (de) | 1973-01-25 |
| DE2215409B2 DE2215409B2 (de) | 1980-02-14 |
| DE2215409C3 true DE2215409C3 (de) | 1980-10-09 |
Family
ID=19812895
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2215409A Expired DE2215409C3 (de) | 1971-04-09 | 1972-03-29 | Halogen-nitro-2,2'methylendiphenole, ihre Salze und Ester, Verfahren zu ihrer Herstellung und ihre Verwendung |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3884906A (cg-RX-API-DMAC10.html) |
| JP (2) | JPS5525177B1 (cg-RX-API-DMAC10.html) |
| AR (2) | AR194587A1 (cg-RX-API-DMAC10.html) |
| AU (1) | AU459272B2 (cg-RX-API-DMAC10.html) |
| BE (1) | BE781674A (cg-RX-API-DMAC10.html) |
| CH (2) | CH575372A5 (cg-RX-API-DMAC10.html) |
| DE (1) | DE2215409C3 (cg-RX-API-DMAC10.html) |
| DK (1) | DK143227C (cg-RX-API-DMAC10.html) |
| ES (1) | ES401501A1 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2132788B1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1346266A (cg-RX-API-DMAC10.html) |
| HU (1) | HU165790B (cg-RX-API-DMAC10.html) |
| IE (1) | IE36209B1 (cg-RX-API-DMAC10.html) |
| IL (1) | IL39108A (cg-RX-API-DMAC10.html) |
| NL (1) | NL167151C (cg-RX-API-DMAC10.html) |
| PH (2) | PH15268A (cg-RX-API-DMAC10.html) |
| SE (1) | SE389331B (cg-RX-API-DMAC10.html) |
| SU (1) | SU580828A3 (cg-RX-API-DMAC10.html) |
| ZA (1) | ZA722331B (cg-RX-API-DMAC10.html) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU4101678A (en) * | 1977-11-08 | 1980-05-01 | Ici Australia Ltd | Process for killing parasites |
| FR2549476B1 (fr) * | 1983-07-20 | 1986-04-25 | Rech Ind | Benzyl-phenyl-osides, procede de preparation et utilisation en therapeutique |
| US6403652B1 (en) | 2000-06-30 | 2002-06-11 | Colgate-Palmolive Company | Method and composition |
| IL218714A (en) * | 2004-03-16 | 2013-02-28 | Boehringer Ingelheim Int | Glucopyranosyl-substituted benzol derivatives, drugs containing said compounds, the use thereof and method for the production thereof |
| UA91546C2 (uk) * | 2005-05-03 | 2010-08-10 | Бьорінгер Інгельхайм Інтернаціональ Гмбх | КРИСТАЛІЧНА ФОРМА 1-ХЛОР-4-(β-D-ГЛЮКОПІРАНОЗ-1-ИЛ)-2-[4-((S)-ТЕТРАГІДРОФУРАН-3-ІЛОКСИ)-БЕНЗИЛ]-БЕНЗОЛУ, СПОСІБ ЇЇ ОДЕРЖАННЯ ТА ЇЇ ЗАСТОСУВАННЯ ПРИ ПРИГОТУВАННІ ЛІКАРСЬКИХ ЗАСОБІВ |
| US7772191B2 (en) | 2005-05-10 | 2010-08-10 | Boehringer Ingelheim International Gmbh | Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives and intermediates therein |
| PE20080697A1 (es) * | 2006-05-03 | 2008-08-05 | Boehringer Ingelheim Int | Derivados de benzonitrilo sustituidos con glucopiranosilo, composiciones farmaceuticas que contienen compuestos de este tipo, su uso y procedimiento para su fabricacion |
| CL2008002427A1 (es) * | 2007-08-16 | 2009-09-11 | Boehringer Ingelheim Int | Composicion farmaceutica que comprende 1-cloro-4-(b-d-glucopiranos-1-il)-2-[4-((s)-tetrahidrofurano-3-iloxi)bencil]-benceno combinado con 1-[(4-metilquinazolin-2-il)metil]-3-metil-7-(2-butin-1-il)-8-(3-(r)-aminopiperidin-1-il)xantina; y su uso para tratar diabetes mellitus tipo 2. |
| WO2009068617A1 (en) * | 2007-11-30 | 2009-06-04 | Boehringer Ingelheim International Gmbh | 1, 5-dihydro-pyrazolo (3, 4-d) pyrimidin-4-one derivatives and their use as pde9a modulators for the teatment of cns disorders |
| UA105362C2 (en) * | 2008-04-02 | 2014-05-12 | Бьорингер Ингельхайм Интернациональ Гмбх | 1-heterocyclyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their use as pde9a modulators |
| MX2011002340A (es) | 2008-09-08 | 2011-04-04 | Boehringer Ingelheim Int | Pirazolopirimidinas y su uso para el tratamiento de trastornos del snc. |
| JP5685550B2 (ja) | 2009-02-13 | 2015-03-18 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｓｇｌｔ２阻害剤、ｄｐｐ−ｉｖ阻害剤、更に必要により抗糖尿病薬を含む医薬組成物及びその使用 |
| HRP20240365T1 (hr) * | 2009-02-13 | 2024-06-07 | Boehringer Ingelheim International Gmbh | Farmaceutski pripravak koji sadrži derivate glukopiranozil difenilmetana, njegov farmaceutski oblik za doziranje, postupak za njihovu proizvodnju i njihove uporabe za poboljšanu regulaciju glikemije kod pacijenta |
| MX344264B (es) | 2009-02-13 | 2016-12-09 | Boehringer Ingelheim Int Gmbh * | Inhibidor de sglt-2 para el tratamiento de diabetes mellitus tipo 1, diabetes mellitus tipo 2, tolerancia deteriorada a la glucosa o hiperglucemia. |
| BRPI1011533A2 (pt) * | 2009-03-31 | 2016-03-29 | Boehringer Ingelheim Int | derivados de 1-heterocicil-1 5- diidro-pirazolo [3,4--d] pirimidin-4-ona e seu uso como moduladores de pde9a. |
| TW201118099A (en) * | 2009-08-12 | 2011-06-01 | Boehringer Ingelheim Int | New compounds for the treatment of CNS disorders |
| AU2010303123B2 (en) * | 2009-09-30 | 2014-02-27 | Boehringer Ingelheim International Gmbh | Method for the preparation of a crystalline form of 1-chloro-4- (Beta-D-glucopyranos-1-yl)-2-(4-((S)-tetrahydrofuran-3-yloxy)benzyl)benzene |
| HUE026133T2 (en) | 2009-09-30 | 2016-05-30 | Boehringer Ingelheim Int | Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives |
| UY32919A (es) * | 2009-10-02 | 2011-04-29 | Boehringer Ingelheim Int | Composición farmacéutica, forma de dosificación farmacéutica, procedimiento para su preparación, mé todos para su tratamiento y sus usos |
| AP2012006631A0 (en) | 2010-08-12 | 2012-12-31 | Boehringer Ingelheim Int | 6-Cycloalkyl-1, 5-dihydro-pyrazolo[3,4-D] pyrimidin-4-one derivatives and their use as PDE9A inhibitors |
| US8809345B2 (en) | 2011-02-15 | 2014-08-19 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-pyrazolopyrimidinones for the treatment of CNS disorders |
| UY33937A (es) | 2011-03-07 | 2012-09-28 | Boehringer Ingelheim Int | Composiciones farmacéuticas que contienen inhibidores de dpp-4 y/o sglt-2 y metformina |
| US9555001B2 (en) | 2012-03-07 | 2017-01-31 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition and uses thereof |
| US9192617B2 (en) | 2012-03-20 | 2015-11-24 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| HK1215398A1 (zh) | 2013-04-05 | 2016-08-26 | 勃林格殷格翰国际有限公司 | 依帕列净的治疗用途 |
| US11813275B2 (en) | 2013-04-05 | 2023-11-14 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| US20140303097A1 (en) | 2013-04-05 | 2014-10-09 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| CA2812519A1 (en) | 2013-04-05 | 2014-10-05 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| PT2986304T (pt) | 2013-04-18 | 2022-02-25 | Boehringer Ingelheim Int | Composição farmacêutica, métodos para o tratamento e suas utilizações |
| MA46742A (fr) | 2016-11-10 | 2019-09-18 | Boehringer Ingelheim Int | Composition pharmaceutique, méthodes de traitement et leurs utilisations |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2544826A (en) * | 1945-05-08 | 1951-03-13 | Dow Chemical Co | Anthelmintic feed composition |
| US2615052A (en) * | 1950-06-23 | 1952-10-21 | Allied Lab Inc | 2,2'-methylenebis(4-chloro-6-nitrophenol) and a method for its production |
| US2739941A (en) * | 1952-09-13 | 1956-03-27 | Gen Aniline & Film Corp | Germicidal soap composition |
| NL283922A (cg-RX-API-DMAC10.html) * | 1962-10-03 |
-
1971
- 1971-04-09 NL NL7104839.A patent/NL167151C/xx not_active IP Right Cessation
-
1972
- 1972-03-21 IE IE364/72A patent/IE36209B1/xx unknown
- 1972-03-24 GB GB1405372A patent/GB1346266A/en not_active Expired
- 1972-03-29 US US239341A patent/US3884906A/en not_active Expired - Lifetime
- 1972-03-29 IL IL39108A patent/IL39108A/en unknown
- 1972-03-29 DE DE2215409A patent/DE2215409C3/de not_active Expired
- 1972-04-05 AR AR241303A patent/AR194587A1/es active
- 1972-04-05 BE BE781674A patent/BE781674A/xx not_active IP Right Cessation
- 1972-04-06 AU AU40850/72A patent/AU459272B2/en not_active Expired
- 1972-04-06 ES ES401501A patent/ES401501A1/es not_active Expired
- 1972-04-07 SU SU7201770201A patent/SU580828A3/ru active
- 1972-04-07 SE SE7204544A patent/SE389331B/xx unknown
- 1972-04-07 DK DK170572A patent/DK143227C/da not_active IP Right Cessation
- 1972-04-07 HU HUCE872A patent/HU165790B/hu unknown
- 1972-04-07 PH PH13428A patent/PH15268A/en unknown
- 1972-04-07 FR FR7212355A patent/FR2132788B1/fr not_active Expired
- 1972-04-07 ZA ZA722331A patent/ZA722331B/xx unknown
- 1972-04-08 JP JP3487172A patent/JPS5525177B1/ja active Pending
- 1972-04-10 CH CH1324975A patent/CH575372A5/xx not_active IP Right Cessation
- 1972-04-10 CH CH524572A patent/CH586182A5/xx not_active IP Right Cessation
-
1973
- 1973-02-26 AR AR246797A patent/AR193590A1/es active
-
1975
- 1975-02-24 PH PH16845A patent/PH14191A/en unknown
-
1978
- 1978-08-23 JP JP53101920A patent/JPS5950645B2/ja not_active Expired
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