DE2322779A1 - Benzophenon-derivate und verfahren zu ihrer herstellung - Google Patents
Benzophenon-derivate und verfahren zu ihrer herstellungInfo
- Publication number
- DE2322779A1 DE2322779A1 DE2322779A DE2322779A DE2322779A1 DE 2322779 A1 DE2322779 A1 DE 2322779A1 DE 2322779 A DE2322779 A DE 2322779A DE 2322779 A DE2322779 A DE 2322779A DE 2322779 A1 DE2322779 A1 DE 2322779A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- benzophenone
- methyl
- benzophenone derivatives
- radical
- 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
- 238000000034 method Methods 0.000 title claims description 7
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical class C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000000460 chlorine Substances 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 25
- -1 methylmercapto Chemical group 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 12
- 150000008366 benzophenones Chemical class 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 150000002576 ketones Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 3
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- 238000003756 stirring Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 229940024874 benzophenone Drugs 0.000 description 5
- 239000012965 benzophenone Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 4
- 241000251730 Chondrichthyes Species 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000013016 damping Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- CPLWKNRPZVNELG-UHFFFAOYSA-N (3-chlorophenyl)-phenylmethanone Chemical compound ClC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 CPLWKNRPZVNELG-UHFFFAOYSA-N 0.000 description 2
- INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000009194 climbing Effects 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- GRDGBWVSVMLKBV-UHFFFAOYSA-N (2-amino-5-nitrophenyl)-(2-chlorophenyl)methanone Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1Cl GRDGBWVSVMLKBV-UHFFFAOYSA-N 0.000 description 1
- RGWUYUDLSVKMDI-UHFFFAOYSA-N 2-(1-ethylcyclohexyl)acetic acid Chemical compound OC(=O)CC1(CC)CCCCC1 RGWUYUDLSVKMDI-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- LRSAABGELCWWNT-UHFFFAOYSA-N 2-[[2-(2-benzoyl-4-chloroanilino)-2-oxoethyl]-methylamino]acetic acid;hydrochloride Chemical compound Cl.OC(=O)CN(C)CC(=O)NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 LRSAABGELCWWNT-UHFFFAOYSA-N 0.000 description 1
- MDRIRFWZWGSGFC-UHFFFAOYSA-N 2-methyl-3-(methylamino)propanenitrile Chemical compound CNCC(C)C#N MDRIRFWZWGSGFC-UHFFFAOYSA-N 0.000 description 1
- YXKJDSILZUNOIQ-UHFFFAOYSA-N 2-methyl-3-(methylamino)propanenitrile;hydrochloride Chemical compound Cl.CNCC(C)C#N YXKJDSILZUNOIQ-UHFFFAOYSA-N 0.000 description 1
- YUOMYYHJZHVWDF-UHFFFAOYSA-N 3-aminobutanenitrile;hydrochloride Chemical compound Cl.CC(N)CC#N YUOMYYHJZHVWDF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- LCNHBFJYBHBWBL-UHFFFAOYSA-N C(#N)CCCN(CC(=O)NC1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)Cl)C Chemical compound C(#N)CCCN(CC(=O)NC1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)Cl)C LCNHBFJYBHBWBL-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- GTNGBHWYALUTBM-UHFFFAOYSA-N diphenylmethanone;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(=O)C1=CC=CC=C1 GTNGBHWYALUTBM-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229960004815 meprobamate Drugs 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000008030 superplasticizer Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU65340 | 1972-05-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2322779A1 true DE2322779A1 (de) | 1973-11-22 |
Family
ID=19727041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2322779A Pending DE2322779A1 (de) | 1972-05-12 | 1973-05-05 | Benzophenon-derivate und verfahren zu ihrer herstellung |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3888899A (en, 2012) |
| JP (1) | JPS4948644A (en, 2012) |
| AR (3) | AR196348A1 (en, 2012) |
| AT (3) | AT324309B (en, 2012) |
| AU (1) | AU475851B2 (en, 2012) |
| BE (1) | BE799222A (en, 2012) |
| CA (1) | CA1010891A (en, 2012) |
| CH (3) | CH573398A5 (en, 2012) |
| CS (3) | CS176235B2 (en, 2012) |
| DD (1) | DD107439A5 (en, 2012) |
| DE (1) | DE2322779A1 (en, 2012) |
| ES (3) | ES414708A1 (en, 2012) |
| FR (1) | FR2184739B1 (en, 2012) |
| GB (1) | GB1377312A (en, 2012) |
| HU (1) | HU167099B (en, 2012) |
| IE (1) | IE37616B1 (en, 2012) |
| IL (1) | IL42189A (en, 2012) |
| LU (1) | LU65340A1 (en, 2012) |
| NL (1) | NL7305968A (en, 2012) |
| PH (1) | PH9698A (en, 2012) |
| RO (3) | RO63455A (en, 2012) |
| SU (3) | SU508176A3 (en, 2012) |
| ZA (1) | ZA733221B (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2356239A1 (de) * | 1973-11-10 | 1975-05-15 | Cassella Farbwerke Mainkur Ag | Benzophenon-derivate und verfahren zu ihrer herstellung |
| US4025551A (en) * | 1974-02-14 | 1977-05-24 | G. D. Searle & Co. | 3-Amino-N-substituted succinamic acids |
| FR2436776A1 (fr) * | 1978-09-25 | 1980-04-18 | Fabre Sa Pierre | Nouveaux derives d'ortho chloro benzoyl-2 chloro-4 glycylanilide, leur preparation et leur application en tant que medicaments |
| JPS55171444U (en, 2012) * | 1979-05-21 | 1980-12-09 | ||
| FR2459793A1 (fr) * | 1979-06-25 | 1981-01-16 | Fabre Sa Pierre | Nouveaux derives de benzoyl-2 nitro-4 anilides, leur preparation et leur application en tant que medicaments |
| US4891058A (en) * | 1988-07-18 | 1990-01-02 | Ici Americas Inc. | 1-alkyl-3-aryl imidazolidine-2,4-diones and herbicidal use |
| US4944796A (en) * | 1988-11-14 | 1990-07-31 | Ici Americas Inc. | Certain 2-(disubstituted amino) acetanilide herbicides |
| US5298033A (en) * | 1989-03-14 | 1994-03-29 | Ciba-Geigy Corporation | Ultraviolet absorbing lenses and methods of manufacturing thereof |
| JP2566855B2 (ja) * | 1991-07-08 | 1996-12-25 | 月島食品工業株式会社 | 油脂組成物 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL221898A (en, 2012) * | 1956-10-25 | |||
| US3455985A (en) * | 1961-06-16 | 1969-07-15 | Hoffmann La Roche | 2-(alpha-amino-lower alkanoyl amino)benzophenones |
| US3914215A (en) * | 1967-11-27 | 1975-10-21 | Sankyo Co | Benzodiazepine derivatives and process for preparing the same |
-
1972
- 1972-05-12 LU LU65340A patent/LU65340A1/xx unknown
-
1973
- 1973-04-27 NL NL7305968A patent/NL7305968A/xx not_active Application Discontinuation
- 1973-05-03 IL IL42189A patent/IL42189A/en unknown
- 1973-05-04 GB GB2129573A patent/GB1377312A/en not_active Expired
- 1973-05-05 DE DE2322779A patent/DE2322779A1/de active Pending
- 1973-05-07 BE BE130856A patent/BE799222A/xx unknown
- 1973-05-08 US US358455A patent/US3888899A/en not_active Expired - Lifetime
- 1973-05-08 IE IE728/73A patent/IE37616B1/xx unknown
- 1973-05-09 RO RO7300077146A patent/RO63455A/ro unknown
- 1973-05-09 RO RO7300074726A patent/RO63440A/ro unknown
- 1973-05-09 CA CA170,800A patent/CA1010891A/en not_active Expired
- 1973-05-09 RO RO7300077145A patent/RO63686A/ro unknown
- 1973-05-10 JP JP48051239A patent/JPS4948644A/ja active Pending
- 1973-05-10 PH PH14602*UA patent/PH9698A/en unknown
- 1973-05-10 DD DD170763A patent/DD107439A5/xx unknown
- 1973-05-11 CH CH673673A patent/CH573398A5/xx not_active IP Right Cessation
- 1973-05-11 FR FR7317146A patent/FR2184739B1/fr not_active Expired
- 1973-05-11 ZA ZA733221A patent/ZA733221B/xx unknown
- 1973-05-11 AR AR247999A patent/AR196348A1/es active
- 1973-05-11 AR AR247998A patent/AR196347A1/es active
- 1973-05-11 CS CS3390A patent/CS176235B2/cs unknown
- 1973-05-11 AT AT415773A patent/AT324309B/de not_active IP Right Cessation
- 1973-05-11 CS CS3388A patent/CS176233B2/cs unknown
- 1973-05-11 SU SU1920009A patent/SU508176A3/ru active
- 1973-05-11 AR AR247997A patent/AR196346A1/es active
- 1973-05-11 HU HUCA345A patent/HU167099B/hu unknown
- 1973-05-11 AT AT415873A patent/AT324310B/de not_active IP Right Cessation
- 1973-05-11 CS CS3389A patent/CS176234B2/cs unknown
- 1973-05-11 SU SU1920008A patent/SU467517A3/ru active
- 1973-05-11 AU AU55572/73A patent/AU475851B2/en not_active Expired
- 1973-05-11 SU SU1920007A patent/SU517252A3/ru active
- 1973-05-11 CH CH673773A patent/CH590215A5/xx not_active IP Right Cessation
- 1973-05-11 AT AT415973A patent/AT324311B/de not_active IP Right Cessation
- 1973-05-11 CH CH673573A patent/CH573397A5/xx not_active IP Right Cessation
- 1973-05-12 ES ES414708A patent/ES414708A1/es not_active Expired
- 1973-05-12 ES ES414706A patent/ES414706A1/es not_active Expired
- 1973-05-12 ES ES414707A patent/ES414707A1/es not_active Expired
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