DE2546738C2 - Substituierte 2-Hydroxy-benzophenone und sie enthaltende Arzneimittel - Google Patents
Substituierte 2-Hydroxy-benzophenone und sie enthaltende ArzneimittelInfo
- Publication number
- DE2546738C2 DE2546738C2 DE2546738A DE2546738A DE2546738C2 DE 2546738 C2 DE2546738 C2 DE 2546738C2 DE 2546738 A DE2546738 A DE 2546738A DE 2546738 A DE2546738 A DE 2546738A DE 2546738 C2 DE2546738 C2 DE 2546738C2
- Authority
- DE
- Germany
- Prior art keywords
- hydroxy
- ethyl
- substituted
- benzophenones
- mol
- 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
- 239000003814 drug Chemical class 0.000 title claims description 12
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 title claims description 11
- 229940079593 drug Drugs 0.000 title description 4
- 239000000460 chlorine Substances 0.000 claims description 15
- 150000008366 benzophenones Chemical class 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 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
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 39
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- -1 polypropylene Polymers 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000012965 benzophenone Substances 0.000 description 9
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 8
- 206010020751 Hypersensitivity Diseases 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 208000026935 allergic disease Diseases 0.000 description 6
- 208000006673 asthma Diseases 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 230000003266 anti-allergic effect Effects 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 210000004072 lung Anatomy 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 241000700199 Cavia porcellus Species 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- 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 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000007815 allergy Effects 0.000 description 4
- 239000000924 antiasthmatic agent Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- GAUNQDRIMAOCSY-UHFFFAOYSA-N (4-chlorophenyl)-(2-hydroxy-5-propylphenyl)methanone Chemical compound CCCC1=CC=C(O)C(C(=O)C=2C=CC(Cl)=CC=2)=C1 GAUNQDRIMAOCSY-UHFFFAOYSA-N 0.000 description 3
- RFOOIXAAMPCURS-UHFFFAOYSA-N (4-chlorophenyl)-(4-ethyl-2-hydroxyphenyl)methanone Chemical compound OC1=CC(CC)=CC=C1C(=O)C1=CC=C(Cl)C=C1 RFOOIXAAMPCURS-UHFFFAOYSA-N 0.000 description 3
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 3
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 3
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical group FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 3
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 3
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 3
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 230000009610 hypersensitivity Effects 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- RTAQNUUHINNFBO-UHFFFAOYSA-N (4-chlorophenyl)-(2-hydroxy-3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)C=2C=CC(Cl)=CC=2)=C1O RTAQNUUHINNFBO-UHFFFAOYSA-N 0.000 description 2
- IJQDGZBYOCHMOW-UHFFFAOYSA-N (4-chlorophenyl)-(3-ethyl-2-hydroxyphenyl)methanone Chemical compound CCC1=CC=CC(C(=O)C=2C=CC(Cl)=CC=2)=C1O IJQDGZBYOCHMOW-UHFFFAOYSA-N 0.000 description 2
- XMLUJUUALYEAIU-UHFFFAOYSA-N (4-chlorophenyl)-(5-ethyl-2-hydroxyphenyl)methanone Chemical compound CCC1=CC=C(O)C(C(=O)C=2C=CC(Cl)=CC=2)=C1 XMLUJUUALYEAIU-UHFFFAOYSA-N 0.000 description 2
- CEOCVKWBUWKBKA-UHFFFAOYSA-N 2,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1Cl CEOCVKWBUWKBKA-UHFFFAOYSA-N 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical compound CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 230000001088 anti-asthma Effects 0.000 description 2
- 239000012223 aqueous fraction Substances 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000004452 microanalysis Methods 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
- 239000004296 sodium metabisulphite Substances 0.000 description 2
- 235000010262 sodium metabisulphite Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- PBNAXPINULHPCD-UHFFFAOYSA-N (2,4-dichlorophenyl)-(3-ethyl-2-hydroxyphenyl)methanone Chemical compound CCC1=CC=CC(C(=O)C=2C(=CC(Cl)=CC=2)Cl)=C1O PBNAXPINULHPCD-UHFFFAOYSA-N 0.000 description 1
- ABYUAQZLHDPGGX-UHFFFAOYSA-N (2,4-dichlorophenyl)-(5-ethyl-2-hydroxyphenyl)methanone Chemical compound CCC1=CC=C(O)C(C(=O)C=2C(=CC(Cl)=CC=2)Cl)=C1 ABYUAQZLHDPGGX-UHFFFAOYSA-N 0.000 description 1
- VXVDDGRYEWTFTP-UHFFFAOYSA-N (2-chlorophenyl)-(5-ethyl-2-hydroxyphenyl)methanone Chemical compound CCC1=CC=C(O)C(C(=O)C=2C(=CC=CC=2)Cl)=C1 VXVDDGRYEWTFTP-UHFFFAOYSA-N 0.000 description 1
- OTSCGWVXBUNNFU-UHFFFAOYSA-N (2-hydroxy-5-methylphenyl)-(4-nitrophenyl)methanone Chemical compound CC1=CC=C(O)C(C(=O)C=2C=CC(=CC=2)[N+]([O-])=O)=C1 OTSCGWVXBUNNFU-UHFFFAOYSA-N 0.000 description 1
- CUNWUEBNSZSNRX-RKGWDQTMSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;(z)-octadec-9-enoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O CUNWUEBNSZSNRX-RKGWDQTMSA-N 0.000 description 1
- GEZIUOUTPVCCAA-UHFFFAOYSA-N (3,4-dichlorophenyl)-(5-ethyl-2-hydroxyphenyl)methanone Chemical compound CCC1=CC=C(O)C(C(=O)C=2C=C(Cl)C(Cl)=CC=2)=C1 GEZIUOUTPVCCAA-UHFFFAOYSA-N 0.000 description 1
- CPAQCHCZPMVQSV-UHFFFAOYSA-N (3-chlorophenyl)-(4-ethyl-2-hydroxyphenyl)methanone Chemical compound OC1=CC(CC)=CC=C1C(=O)C1=CC=CC(Cl)=C1 CPAQCHCZPMVQSV-UHFFFAOYSA-N 0.000 description 1
- VQSPPOBWGMJCIP-UHFFFAOYSA-N (3-chlorophenyl)-(5-ethyl-2-hydroxyphenyl)methanone Chemical compound CCC1=CC=C(O)C(C(=O)C=2C=C(Cl)C=CC=2)=C1 VQSPPOBWGMJCIP-UHFFFAOYSA-N 0.000 description 1
- VVNDADICXKIBDN-UHFFFAOYSA-N (4-bromophenyl)-(5-ethyl-2-hydroxyphenyl)methanone Chemical compound CCC1=CC=C(O)C(C(=O)C=2C=CC(Br)=CC=2)=C1 VVNDADICXKIBDN-UHFFFAOYSA-N 0.000 description 1
- RHSZXOZMBKLBNS-UHFFFAOYSA-N (4-chlorophenyl)-(2-ethyl-4-hydroxyphenyl)methanone Chemical compound CCC1=CC(O)=CC=C1C(=O)C1=CC=C(Cl)C=C1 RHSZXOZMBKLBNS-UHFFFAOYSA-N 0.000 description 1
- NYIGXQMZIRVMDZ-UHFFFAOYSA-N (4-chlorophenyl)-(2-hydroxy-3-propylphenyl)methanone Chemical compound CCCC1=CC=CC(C(=O)C=2C=CC(Cl)=CC=2)=C1O NYIGXQMZIRVMDZ-UHFFFAOYSA-N 0.000 description 1
- BHNLPBBNKQGNGV-UHFFFAOYSA-N (4-ethyl-2-hydroxyphenyl)-(3-fluorophenyl)methanone Chemical compound OC1=CC(CC)=CC=C1C(=O)C1=CC=CC(F)=C1 BHNLPBBNKQGNGV-UHFFFAOYSA-N 0.000 description 1
- DSFXXBFQRNYHCB-UHFFFAOYSA-N (5-butyl-2-hydroxyphenyl)-(4-chlorophenyl)methanone Chemical compound CCCCC1=CC=C(O)C(C(=O)C=2C=CC(Cl)=CC=2)=C1 DSFXXBFQRNYHCB-UHFFFAOYSA-N 0.000 description 1
- LTDGNBAJRYLCBN-UHFFFAOYSA-N (5-ethyl-2-hydroxyphenyl)-(4-methylphenyl)methanone Chemical compound CCC1=CC=C(O)C(C(=O)C=2C=CC(C)=CC=2)=C1 LTDGNBAJRYLCBN-UHFFFAOYSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- GPZXFICWCMCQPF-UHFFFAOYSA-N 2-methylbenzoyl chloride Chemical compound CC1=CC=CC=C1C(Cl)=O GPZXFICWCMCQPF-UHFFFAOYSA-N 0.000 description 1
- VTXNOVCTHUBABW-UHFFFAOYSA-N 3,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C(Cl)=C1 VTXNOVCTHUBABW-UHFFFAOYSA-N 0.000 description 1
- WHIHIKVIWVIIER-UHFFFAOYSA-N 3-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(Cl)=C1 WHIHIKVIWVIIER-UHFFFAOYSA-N 0.000 description 1
- HRXFVWIWXNCVQO-UHFFFAOYSA-N 3-ethyl-2-hydroxybenzoyl chloride Chemical compound CCC1=CC=CC(C(Cl)=O)=C1O HRXFVWIWXNCVQO-UHFFFAOYSA-N 0.000 description 1
- SYVNVEGIRVXRQH-UHFFFAOYSA-N 3-fluorobenzoyl chloride Chemical compound FC1=CC=CC(C(Cl)=O)=C1 SYVNVEGIRVXRQH-UHFFFAOYSA-N 0.000 description 1
- KLSLBUSXWBJMEC-UHFFFAOYSA-N 4-Propylphenol Chemical compound CCCC1=CC=C(O)C=C1 KLSLBUSXWBJMEC-UHFFFAOYSA-N 0.000 description 1
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
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- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
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- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
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- 229920001213 Polysorbate 20 Polymers 0.000 description 1
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- 239000004147 Sorbitan trioleate Substances 0.000 description 1
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 1
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- 229930006000 Sucrose Natural products 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 240000006474 Theobroma bicolor Species 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
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- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000010210 aluminium Nutrition 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
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- 239000000378 calcium silicate Substances 0.000 description 1
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- 235000012241 calcium silicate Nutrition 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical class [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 229940042935 dichlorodifluoromethane Drugs 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229940076230 magnesium sulfate monohydrate Drugs 0.000 description 1
- 229940091250 magnesium supplement Drugs 0.000 description 1
- LFCFXZHKDRJMNS-UHFFFAOYSA-L magnesium;sulfate;hydrate Chemical compound O.[Mg+2].[O-]S([O-])(=O)=O LFCFXZHKDRJMNS-UHFFFAOYSA-L 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000003169 respiratory stimulant agent Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- FTOIWNMPZLTPNQ-UHFFFAOYSA-M sodium 5-(2-hydroxypropoxy)-4-oxochromene-2-carboxylate Chemical compound [Na+].C(=O)([O-])C=1OC2=CC=CC(=C2C(C=1)=O)OCC(C)O FTOIWNMPZLTPNQ-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 229960005078 sorbitan sesquioleate Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000012058 sterile packaged powder Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
- C07C65/40—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups containing singly bound oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB15805/75A GB1549171A (en) | 1975-04-17 | 1975-04-17 | Pharmaceutical formulations containing hydrocy bezophenonederivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2546738A1 DE2546738A1 (de) | 1976-10-28 |
| DE2546738C2 true DE2546738C2 (de) | 1985-12-12 |
Family
ID=10065798
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2546738A Expired DE2546738C2 (de) | 1975-04-17 | 1975-10-18 | Substituierte 2-Hydroxy-benzophenone und sie enthaltende Arzneimittel |
| DE19762615487 Withdrawn DE2615487A1 (de) | 1975-04-17 | 1976-04-09 | Benzophenonderivate, verfahren zu ihrer herstellung und benzophenonderivate enthaltenden arzneimittel |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762615487 Withdrawn DE2615487A1 (de) | 1975-04-17 | 1976-04-09 | Benzophenonderivate, verfahren zu ihrer herstellung und benzophenonderivate enthaltenden arzneimittel |
Country Status (35)
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2377202A2 (fr) * | 1977-01-12 | 1978-08-11 | Pharmascience Lab | Compositions pharmaceutiques contenant de l'hexahydroxy-2,3,4,3',4',5'-benzophenone |
| JPS6197240A (ja) * | 1984-10-16 | 1986-05-15 | Sankyo Kasei Kk | ポリハイドロキシベンゾフエノンの製造法 |
| GB8603578D0 (en) * | 1986-02-13 | 1986-03-19 | Ici Plc | Aromatic ketone |
| LU86387A1 (fr) * | 1986-04-04 | 1987-12-07 | Oreal | Composes aromatiques,leur procede de preparation et leur utilisation en medicine humaine et veterinaire et en cosmetique |
| FR2649975B1 (fr) * | 1989-07-19 | 1991-11-22 | Inst Nat Rech Chimique | Nouveaux derives acetyleniques, leur procede de preparation, nouveaux polymeres acetyleniques et leurs applications |
| US5780676A (en) * | 1992-04-22 | 1998-07-14 | Ligand Pharmaceuticals Incorporated | Compounds having selective activity for Retinoid X Receptors, and means for modulation of processes mediated by Retinoid X Receptors |
| US5962731A (en) * | 1992-04-22 | 1999-10-05 | Ligand Pharmaceuticals Incorporated | Compounds having selective activity for retinoid X receptors, and means for modulation of processes mediated by retinoid X receptors |
| BR9306284A (pt) * | 1992-04-22 | 1998-01-13 | Ligand Pharm Inc | Compostos tendo seletividade pra receptores de retinóides x |
| US7655699B1 (en) | 1992-04-22 | 2010-02-02 | Eisai Inc. | Compounds having selective activity for retinoid X receptors, and means for modulation of processes mediated by retinoid X receptors |
| WO1994015901A1 (en) * | 1993-01-11 | 1994-07-21 | Ligand Pharmaceuticals Inc. | Compounds having selectivity for retinoid x receptors |
| GB9620202D0 (en) * | 1996-09-27 | 1996-11-13 | Rhone Poulenc Agriculture | New herbicides |
| GB2446397A (en) * | 2007-02-06 | 2008-08-13 | Gharda Chemicals Ltd | Improved processes for the production of poly(ether ketone) - PEK - and its monomer |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1060855A (en) * | 1963-09-20 | 1967-03-08 | Ici Ltd | Substituted aromatic ketones |
| CH503463A (de) * | 1969-07-17 | 1971-02-28 | Ciba Geigy Ag | Verwendung von 2-Hydroxybenzophenonen zur Bekämpfung schädlicher Mikroorganismen ausserhalb der Textilindustrie |
| CH515871A (de) * | 1969-07-25 | 1971-11-30 | Sandoz Ag | Verfahren zur Herstellung von neuen 2-Hydroxy-3,5-tert.butyl-benzophenonen |
-
1975
- 1975-04-17 GB GB15805/75A patent/GB1549171A/en not_active Expired
- 1975-10-18 DE DE2546738A patent/DE2546738C2/de not_active Expired
- 1975-10-20 DD DD188946A patent/DD123596A5/xx unknown
-
1976
- 1976-03-19 IE IE586/76A patent/IE42968B1/en unknown
- 1976-03-22 ZA ZA761737A patent/ZA761737B/xx unknown
- 1976-03-23 GR GR50382A patent/GR59849B/el unknown
- 1976-03-24 IL IL49280A patent/IL49280A/xx unknown
- 1976-03-30 DK DK146476A patent/DK146476A/da not_active IP Right Cessation
- 1976-04-01 NZ NZ180379A patent/NZ180379A/xx unknown
- 1976-04-09 NO NO761233A patent/NO146022C/no unknown
- 1976-04-09 DE DE19762615487 patent/DE2615487A1/de not_active Withdrawn
- 1976-04-12 OA OA55796A patent/OA05301A/xx unknown
- 1976-04-12 AR AR262848A patent/AR217399A1/es active
- 1976-04-12 CH CH459876A patent/CH617654A5/fr not_active IP Right Cessation
- 1976-04-13 CA CA250,199A patent/CA1055041A/en not_active Expired
- 1976-04-13 RO RO7685607A patent/RO71258A/ro unknown
- 1976-04-13 ES ES446993A patent/ES446993A1/es not_active Expired
- 1976-04-13 FI FI760999A patent/FI68609C/fi not_active IP Right Cessation
- 1976-04-13 FR FR7610788A patent/FR2307524A1/fr active Granted
- 1976-04-14 PL PL1976188773A patent/PL103084B1/pl unknown
- 1976-04-14 SE SE7604426A patent/SE7604426L/xx not_active Application Discontinuation
- 1976-04-14 PT PT65015A patent/PT65015B/pt unknown
- 1976-04-14 MX MX000173U patent/MX3394E/es unknown
- 1976-04-14 PH PH18332A patent/PH11507A/en unknown
- 1976-04-15 LU LU74773A patent/LU74773A1/xx unknown
- 1976-04-15 CS CS762506A patent/CS196305B2/cs unknown
- 1976-04-15 AT AT278676A patent/AT347430B/de not_active IP Right Cessation
- 1976-04-15 BE BE6045444A patent/BE840826A/xx not_active IP Right Cessation
- 1976-04-16 HU HU76LI288A patent/HU176276B/hu unknown
- 1976-04-16 YU YU00971/76A patent/YU97176A/xx unknown
- 1976-04-16 BG BG032930A patent/BG33275A3/xx unknown
- 1976-04-16 SU SU762345332A patent/SU644372A3/ru active
- 1976-04-17 EG EG76217A patent/EG12255A/xx active
- 1976-04-17 JP JP51044159A patent/JPS51128950A/ja active Pending
- 1976-04-20 NL NL7604164A patent/NL7604164A/xx not_active Application Discontinuation
- 1976-04-20 AU AU13154/76A patent/AU502015B2/en not_active Expired
-
1977
- 1977-08-24 SU SU772514704A patent/SU679133A3/ru active
- 1977-08-25 AT AT617077A patent/AT346829B/de not_active IP Right Cessation
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Representative=s name: TUERK, D., DIPL.-CHEM. DR.RER.NAT. GILLE, C., DIPL |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |