PL63003B1 - - Google Patents

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Publication number: PL63003B1
Authority: PL; Poland
Prior art keywords: solution; ether; phenyl; lower alkyl; dichloroanilino
Prior art date: 1967-10-06

Application number

PL122908A

Other languages

English (en)

Polish (pl)

Original Assignee

J R Geigy A G

Filing date

1967-10-06

Publication date

1971-04-30

1967-10-06 Application filed by J R Geigy A G filed Critical J R Geigy A G

1971-04-30 Publication of PL63003B1 publication Critical patent/PL63003B1/pl

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RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 43
-1 1-piperazinyl Chemical group 0.000 claims description 33
239000002253 acid Substances 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 16
150000002148 esters Chemical class 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 7
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
229910052938 sodium sulfate Inorganic materials 0.000 claims description 5
235000011152 sodium sulphate Nutrition 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 4
238000002844 melting Methods 0.000 claims description 4
239000003208 petroleum Substances 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
238000007792 addition Methods 0.000 claims description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 3
239000001184 potassium carbonate Substances 0.000 claims description 3
229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
238000001816 cooling Methods 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
239000000155 melt Substances 0.000 claims description 2
238000000034 method Methods 0.000 claims description 2
235000019796 monopotassium phosphate Nutrition 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
239000000243 solution Substances 0.000 claims 13
239000007864 aqueous solution Substances 0.000 claims 2
150000002431 hydrogen Chemical group 0.000 claims 2
VETACGBDFVVKGZ-UHFFFAOYSA-N methyl 2-[2-(2,6-dichloroanilino)phenyl]acetate Chemical compound COC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl VETACGBDFVVKGZ-UHFFFAOYSA-N 0.000 claims 2
125000005055 alkyl alkoxy group Chemical group 0.000 claims 1
YXHKONLOYHBTNS-UHFFFAOYSA-N diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
238000003756 stirring Methods 0.000 claims 1
150000007513 acids Chemical class 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
150000001875 compounds Chemical class 0.000 description 9
238000009835 boiling Methods 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
230000000875 corresponding Effects 0.000 description 6
150000001408 amides Chemical class 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
239000000126 substance Substances 0.000 description 4
HDUUZPLYVVQTKN-UHFFFAOYSA-N 2,6-dichloro-N-phenylaniline Chemical compound ClC1=CC=CC(Cl)=C1NC1=CC=CC=C1 HDUUZPLYVVQTKN-UHFFFAOYSA-N 0.000 description 3
LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical class NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 3
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
239000000047 product Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
BZKBCQXYZZXSCO-UHFFFAOYSA-N sodium hydride Chemical compound [H-].[Na+] BZKBCQXYZZXSCO-UHFFFAOYSA-N 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000829 suppository Substances 0.000 description 3
RCWUQXWELSVCCI-UHFFFAOYSA-N 2-[2-(2,6-dichloroanilino)phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl RCWUQXWELSVCCI-UHFFFAOYSA-N 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
DMBHHRLKUKUOEG-UHFFFAOYSA-N Diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
239000001828 Gelatine Substances 0.000 description 2
AMXOYNBUYSYVKV-UHFFFAOYSA-M Lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
206010072736 Rheumatic disease Diseases 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
150000001241 acetals Chemical class 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
230000003110 anti-inflammatory Effects 0.000 description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
239000002775 capsule Substances 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
230000004968 inflammatory condition Effects 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 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
150000004702 methyl esters Chemical class 0.000 description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-Tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 1
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-Bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
ORTTTYFBIZCDQJ-UHFFFAOYSA-N 2-[2-(2,6-dimethylanilino)phenyl]acetamide Chemical compound CC1=CC=CC(C)=C1NC1=CC=CC=C1CC(N)=O ORTTTYFBIZCDQJ-UHFFFAOYSA-N 0.000 description 1
NFOOEIORUZMHKP-UHFFFAOYSA-N 2-[2-(2-chloro-6-methylanilino)phenyl]acetamide Chemical compound CC1=CC=CC(Cl)=C1NC1=CC=CC=C1CC(N)=O NFOOEIORUZMHKP-UHFFFAOYSA-N 0.000 description 1
JGDCJRMXAABYFR-UHFFFAOYSA-N 2-[2-(3-chloro-2-methylanilino)phenyl]acetamide Chemical compound CC1=C(Cl)C=CC=C1NC1=CC=CC=C1CC(N)=O JGDCJRMXAABYFR-UHFFFAOYSA-N 0.000 description 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
GRIXINIGTYIHSN-UHFFFAOYSA-N 2-chloro-N,N-diphenylacetamide Chemical class C=1C=CC=CC=1N(C(=O)CCl)C1=CC=CC=C1 GRIXINIGTYIHSN-UHFFFAOYSA-N 0.000 description 1
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
YJISHJVIRFPGGN-UHFFFAOYSA-N 5-[5-[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy-6-[[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxymethyl]-3,4-dihydroxyoxan-2-yl]oxy-6-(hydroxymethyl)-2-methyloxane-3,4-diol Chemical compound O1C(CO)C(OC)C(O)C(O)C1OCC1C(OC2C(C(O)C(OC)C(CO)O2)O)C(O)C(O)C(OC2C(OC(C)C(O)C2O)CO)O1 YJISHJVIRFPGGN-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N Acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
229920000945 Amylopectin Polymers 0.000 description 1
WMGFVAGNIYUEEP-WUYNJSITSA-N Amylopectin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)O[C@H](OC[C@@H]2[C@H]([C@H](O)[C@@H](O)[C@@H](O[C@@H]3[C@H](O[C@H](O)[C@H](O)[C@H]3O)CO)O2)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@H]1O WMGFVAGNIYUEEP-WUYNJSITSA-N 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N Benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940088623 Biologically Active Substance Drugs 0.000 description 1
210000004369 Blood Anatomy 0.000 description 1
QARVLSVVCXYDNA-UHFFFAOYSA-N Bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L Calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
241000700198 Cavia Species 0.000 description 1
241000207199 Citrus Species 0.000 description 1
BXGJYVHRFZEDND-UHFFFAOYSA-N ClC=1C=CC=C(C1C)NC1=C(C=CC=C1)CC(=O)N(C)C Chemical compound ClC=1C=CC=C(C1C)NC1=C(C=CC=C1)CC(=O)N(C)C BXGJYVHRFZEDND-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-KAZBKCHUSA-N D-Mannitol Natural products OC[C@@H](O)[C@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KAZBKCHUSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N D-sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N Diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
206010015150 Erythema Diseases 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N Ethyl iodide Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
QUPDWYMUPZLYJZ-UHFFFAOYSA-N Ethyl radical Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
102100011343 GLB1 Human genes 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
229940116108 Lactase Drugs 0.000 description 1
108010059881 Lactase Proteins 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
FMVPHKCHGJDQMN-UHFFFAOYSA-N N(C1=CC=CC=C1)C1=C(C=CC=C1)CC#N Chemical class N(C1=CC=CC=C1)C1=C(C=CC=C1)CC#N FMVPHKCHGJDQMN-UHFFFAOYSA-N 0.000 description 1
PKIQYBRRSDPRRI-UHFFFAOYSA-N N(C1=CC=CC=C1)C1=C(CCl)C=CC=C1 Chemical class N(C1=CC=CC=C1)C1=C(CCl)C=CC=C1 PKIQYBRRSDPRRI-UHFFFAOYSA-N 0.000 description 1
CYNYIHKIEHGYOZ-UHFFFAOYSA-N N-Propyl bromide Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N Potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N Sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N Sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
CZMRCDWAGMRECN-GDQSFJPYSA-N Sucrose Natural products O([C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1)[C@@]1(CO)[C@H](O)[C@@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-GDQSFJPYSA-N 0.000 description 1
239000006096 absorbing agent Substances 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
230000002378 acidificating Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000001058 adult Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000006177 alkyl benzyl group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
230000000202 analgesic Effects 0.000 description 1
230000001754 anti-pyretic Effects 0.000 description 1
230000002917 arthritic Effects 0.000 description 1
239000002585 base Substances 0.000 description 1
229940095076 benzaldehyde Drugs 0.000 description 1
239000008280 blood Substances 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
235000020971 citrus fruits Nutrition 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
230000000994 depressed Effects 0.000 description 1
ROSDSFDQCJNGOL-UHFFFAOYSA-N dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drugs Drugs 0.000 description 1
239000000975 dye Substances 0.000 description 1
231100000321 erythema Toxicity 0.000 description 1
KIWBPDUYBMNFTB-UHFFFAOYSA-M ethyl sulfate Chemical compound CCOS([O-])(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-M 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
150000004687 hexahydrates Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000003301 hydrolyzing Effects 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
HPQVWDOOUQVBTO-UHFFFAOYSA-N lithium aluminium hydride Substances [Li+].[Al-] HPQVWDOOUQVBTO-UHFFFAOYSA-N 0.000 description 1
OCZDCIYGECBNKL-UHFFFAOYSA-N lithium;alumanuide Chemical compound [Li+].[AlH4-] OCZDCIYGECBNKL-UHFFFAOYSA-N 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
238000002156 mixing Methods 0.000 description 1
YNAVUWVOSKDBBP-UHFFFAOYSA-N morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
229940113083 morpholine Drugs 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000001264 neutralization Effects 0.000 description 1
150000004993 o-toluidines Chemical group 0.000 description 1
239000003883 ointment base Substances 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N oxo-oxoalumanyloxy-[oxo(oxoalumanyloxy)silyl]oxysilane;dihydrate Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
235000012771 pancakes Nutrition 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
201000003068 rheumatic fever Diseases 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
YOQDYZUWIQVZSF-UHFFFAOYSA-N sodium borohydride Chemical compound [BH4-].[Na+] YOQDYZUWIQVZSF-UHFFFAOYSA-N 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000002511 suppository base 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
230000001225 therapeutic Effects 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
239000002966 varnish Substances 0.000 description 1

PL122908A 1967-10-06 PL63003B1 (fi)

Publications (1)

Publication Number	Publication Date
PL63003B1 true PL63003B1 (fi)	1971-04-30

Publication	Publication Date	Title
US2951082A (en)	1960-08-30	Substituted thiaxanthenes
Okumura et al.	1968	4-Oxo-1, 2, 3, 4-tetrahydroquinazolines. I. Syntheses and pharmacological properties of 2-methyl-3-aryl-4-oxo-1, 2, 3, 4-tetrahydroquinazolines and their 1-acyl derivatives
PL110654B1 (en)	1980-07-31	Method of producing new ethers of hydroxy-benzodiheterocyclic compounds
CA1193264A (en)	1985-09-10	Pharmaceutically active (3-aminopropoxy)bibenzyl derivatives
FI80691C (fi)	1990-07-10	Foerfarande foer framstaellning av bensotiofener och bensofuraner med antiallergisk aktivitet.
IL25708A (en)	1970-03-22	History of benzothiophene and process for their production
FR2459235A1 (fr)	1981-01-09	Nouveaux derives de sulfonyl-aniline, leur procede de preparation et leur application therapeutique
IL25545A (en)	1970-07-19	Transformed phenylacetic acids, their preparation and use
US3155649A (en)	1964-11-03	Benzothiazocinones, related compounds and their preparation
US3043842A (en)	1962-07-10	Substituted acridans
JPS6140674B2 (fi)	1986-09-10
JPH03190872A (ja)	1991-08-20	新規なチオフェン誘導体
US3980652A (en)	1976-09-14	2-(4-Methyl-piperazino)-3 or 5 cyano pyridine
PL99875B1 (pl)	1978-08-31	Sposob wytwarzania nowych oksymow ketonu tienylo wzglednie furylo-fenylo-o-/aminoalkilowego/
EP0592664A1 (en)	1994-04-20	Novel diphenylthyazole derivative
PL128998B1 (en)	1984-03-31	Process for preparing novel 2-amino-3-benzoylphenylacetamides and their derivatives
PL63003B1 (fi)	1971-04-30
US3740394A (en)	1973-06-19	Thiazolo and thiazino pyrimidines
IL27708A (en)	1971-01-28	Substituted o-anilino phenylacetic acid esters and their preparation
US3668206A (en)	1972-06-06	Heterocyclic amine derivatives of 5,8-dihydronaphthyloxy propanols
EP0566288B1 (en)	1995-08-02	Flavone derivatives
US3931173A (en)	1976-01-06	Dioxocin carboxamide derivatives
PL110887B1 (en)	1980-08-30	Method of manufacture of novel 4-substituted 3-sulfamoyl-5-pyrrolylalkylbenzoic acids
US3594388A (en)	1971-07-20	4-amino-5-(substituted phenyl) furazan
CA1085847A (en)	1980-09-16	Piperazine derivatives, a process for their preparation and their applications

PL63003B1 - - Google Patents

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