IL27406A - Stable acid addition salts of bis-(4-hydroxyphenyl)-(quinolyl-2)-methane and their preparation - Google Patents
Stable acid addition salts of bis-(4-hydroxyphenyl)-(quinolyl-2)-methane and their preparationInfo
- Publication number
- IL27406A IL27406A IL2740667A IL2740667A IL27406A IL 27406 A IL27406 A IL 27406A IL 2740667 A IL2740667 A IL 2740667A IL 2740667 A IL2740667 A IL 2740667A IL 27406 A IL27406 A IL 27406A
- Authority
- IL
- Israel
- Prior art keywords
- bis
- methane
- hydroxyphenyl
- quinolyl
- compositions
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 16
- 239000002253 acid Substances 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 8
- 239000000203 mixture Substances 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 239000000829 suppository Substances 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 235000020357 syrup Nutrition 0.000 claims description 2
- 239000006188 syrup Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- -1 iso-quinolyl methanes Chemical class 0.000 description 3
- 230000002475 laxative effect Effects 0.000 description 3
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 244000299461 Theobroma cacao Species 0.000 description 2
- 235000009470 Theobroma cacao Nutrition 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 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
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 239000002511 suppository base Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 1
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- GMACPFCYCYJHOC-UHFFFAOYSA-N [C].C Chemical group [C].C GMACPFCYCYJHOC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Landscapes
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
27406/2 onjam Stable acid addition salts of bis ( -h droxy henyl)-(quinol 1-2)- methane and their preparation DR. KARL THOMAE G.m.b.H.
C: 5996 27406/2 The invention consists in novel acid addition salts of bis-(4-bydroxyphenyl)-(quinolyl-2)-methane having pharmaceutical properties.
The German Patent Specification Ho. 1,081,014 and the British Patent Specification No. 735,683 describe the preparation of bis-(4-hydrophenyl)-quinolyl or iso-quinolyl methanes of the formula wherein Y is a hydroxy, alkoxy or acyloxy group, to are hydrogen or alkyl, aryl, aralkyl, hydroxy, acyloxy or alkoxy groups, R1 is hydrogen or alkyl, and Quin is an unsubstituted or optionally alkyl substituted quinolyl or isoquinolyl radical attached in its 1- or 3- position to the methane carbon atom.
One of the compounds of formula I above thus described is bis-(4-hydroxyphenyl)-(quinolyl-2)«methane which has an excellent laxative activity and also a very low toxicity.
These compounds are prepared by the reaction of a compound of the formula 27406/2 with a phenol or a phenol derivative of the formula Y in the presence of a water removing agent which may be an acid such as sulfuric4 ydrochloric or phosphoric acid, or, for example, zinc chloride, a phosphorus halide, or phosphorus pentoxide, tin tetrachloride, brron trifluoride or aluminium chloride.
These patent specifications do not disclose the existence of salts of the compounds of formula I or the preparation of such salts.
The aforesaid bis-(4-hydroxyphenyl)-(quinolyl-2)~ methane which, in the freshly prepared state, exists as a colourless substance, becomes discoloured on prolonged storage. This decoloration, which is due to a slow modi* fication in the molecule, occurs very rapidly upon treatment with polar solvents, e.g. mixtures of ethanol and water, such as those normally used, for example, for granulation, the preliminary step of the tablet-making process. Formulation of pharmaceutical preparations is thus made very difficult.
It has now been found according to the invention that certain acid addition salts of this compound are considerably more stable than the free base.
The invention, therefore, consists in stable physiologically compatible acid addition salts of bis- 4-h drox hen l - uinol l-2 -methane with inor anic or 27406 2 strong organic acids. These salts are considerably more ^ stable than the free base and possess very good stomach compatabilit . They have a very good laxative action.
Thus, for example, bis-(4-hydroxyphenyl)-(quinolyl-2)-methane hydrochloride has a laxative action on humans at a dose of only 30 mg.
Preferred inorganic acida for the salt formation are hydrochloric acid, hydrobromic acid, sulphuric acid and phosphoric acid, and preferred strong organic acid methanesulphonic acid, jg-toluenesulphonic acid and benzene-sulphonic acid.
The new salts are prepared by reacting the free base with the selected acid.
This reaction is conveniently carried out in an inert organic liquid, preferably a ketone such as acetone, or an alcohol, such as methanol or ethanol.
The invention also consists in pharmaceutical compositions comprising as active ingredient one or more stable physiologically compatible acid addition salts of bis-(4-h droxyphen 1)-( uinoly1-2)-methane together with one or more pharmaceutical carriers or excipients. Such compositions are preferably in the form of dosage units such as tablets, capsules, cachets and suppositories; or otherwise in liquid forms, e.g. syrups, suspensions or elixirs; such liquid forms preferably containing 0.1 to 1.0$ w/v (g/ml) of active ingredient. Since the bis-( -h drox p enyl)-( uinol 1-2)-methane salts are compatible with the stomach, there is no necessity to coat tablets containing these salts to form dragees. Tablets may, however, be therefore advantageously contain 10 to 250 mg. of the active ingredient. Dosage forms for oral administration preferably contain 10 to 60 mg, advantageously 20-40 mg. of active ingredient, while forms for rectal administration preferably contain 50 to 250 mg, for example about 150 mg, of active ingredient.
The following examples illustrate the invention:-Example 1 Bis-(4-hydroxyphenyl)-(quinolyl-2)-methane hydrochloride 40 g. of bis-(4-hydroxyphenyl)-(quinolyl-2)-methane are suspended in 200 ml. of acetone. Hydrogen chloride is passed into the suspension with stirring and cooling until it is saturated. The light-yellow mass of crystals formed is filtered with suction and dried. 39 g. of hydrochloride of m.pt. 205°C are obtained.
The salts stated herebelow were obtained by reaction of bis-(4-hydroxyphenyl)-(quinolyl-2 )methane-in acetone ·ore^lmQl with the corresponding acids: a) acid sulphate m.pt. = 238°C b) methanesulphonate m.pt. = 224°C c) toluenesulphonate m.pt. = 136°C d) benzenesulphonate m.pt. = 138°C e) hydrobromide m.pt. = 218°C f) acid phosphate m.pt. = 226°C The following examples describe the production of several forms of pharmaceutical preparations.
Example 2 Tablets with 40 mg. of bis-(4-hydrox phenyl)-(quinolyl-2 )- bis-(4-hydroxyphenyl)-(quinolyl-2)- ethane hydrochloride 40.0 mg lactose 118,0 mg potato starch 50.0 mg polyvinyl pyrrolidone 9.0 mg tartaric acid 1.0 mg magnesium stea ate 2.0 mg 220.0 mg Method of preparation; A mixture of active substance, lactose and potato starch is granulated through a 1.5 mm sieve with a 15$ aqueous polyvinyl pyrrolidone solution containing the dissolved tartaric acid, dried at 45°C and again granulated through a 1.5 mm sieve. The granulate is mixed with magnesium stearate and then pressed into tablets.
Tablet weight : 220 mg. Die : 9 mm.
Example 3 Suppositories with 150 mg. of bis-(4-hydroxyphenyl)- ( quinoly1-2 )-methane hydrochloride 1 suppository contains: bis-( 4-hydrophenyl) -( quinolyl-2)-methane hydrochloride 150.0 mg suppository base (e.g. Witepsol W 45) 1550.0 mg 1700.0 mg Method of preparation: The suppository base is melted, and brought to a temperature of 37°C. The finely powdered active subs is added thereto with stirring, the mixture cooled to 35°C and the melt poured into pre-cooled suppository Example 4 Suspension with 20 mg. of bis-( 4-hydroxyphenyl )-(quinolyl-2)-methane hydrochloride per 5 ml.
Composition: 100 ml. of suspension contain: bis-( 4-hydroxyphenyl )-( quinolyl-2 )-methane hydrochloride Aerosil Carboxymethyl cellulose (highly viscous) Methyl j)-hydroxybenzoate n-Propyl jD-hydroxybenzoate Cocoa essence Glycerol Sugar Dist. water 115.0 g Method of preparation: The jo-hydroxybenzoates are dissolved in water heated to 80°C, the Aerosil is suspended in this solution and then a mixture of carboxymethyl cellulose and sugar dissolved therein. The mixture is then cooled to room temperature and the finely powdered active substance suspended therein. Glycerol and cocoa essence are then added. 5 ml. of this suspension contain 20 mg. of bis- ( 4-hydroxyphenyl )-( quinolyl-2 )-methane hydrochloride . 27406/2
Claims (4)
1. Stable physiologically compatible acid addition salts of bis-(4-hydroxyphenyl)-(qidjaolyl-2)-methane with inorganic or strong organic acids.
2. Bis-(4-hydroxyphenyl)-(quinolyl-2)-methane hydrochloride
3. Bis-(4-hydrophenyl)-( uinolyl-2 )-me hane hydrogen sulphate.
4. Bis-(4-hydroxyphenyl)-(quinolyl-2)-raethane methane-sulphonate.
5. is-(4-hydroxyphenyl)-(quinolyl-2)-methane toluene-sulphonate.
6. Bis-(4-hydroxyphen 1)-( uinolyl-2)-methane benzenesulphonate.
7. Bis-(4-hydroxyphenyl)-( uinolyl-2)-me hane hydrobromide.
8. Acid bis-(4-hydroxyphenyl)-(quinolyl-2)-methane phosphate.
9. A process for the preparation of physiologically compatible stable acid addition salts of bis-( -hydroxyphenyl)-(quinolyl-2)-methane which comprises treating bis-(4-hydroxyphenyl)-(quinolyl-2)-methane with an inorganic or strong organic acid ^ an inert organic liquid.
10. A process as claimed in Claim 9, in which the organic liquid is ethanol, methanol or acetone.
11. A process as claimed in Claim 9 substantially as 27406/2 herein described with reference to Example 1.
12. Pharmaceutical compositions comprising as an active ingredient one or more acid addition salts as claimed in any one of Claims 1 to 8.
13. Compositions as claimed in Claim 12 in the form of dosage units, e.g. pills, tablets, coated tablets, capsules, cachets, or suppositories.
14. Compositions as claimed in Claim 13, in which each dosage unit contains 10 to 250 mg. of active ingredient. 1^· Orally-administrable compositions as claimed in Claim 14, containing from 10 to 60 mg., preferably 20 to 40 mg., of active ingredient per dosage unit.
16. Compositions as claimed in Claim 14 in the form of suppositories containing from 50 to 250 mg. of active ingredient per dosage unit.
17. Compositions as claimed in Claim 12 in the form of syrups, suspensions or elixirs.
18. Compositions as claimed in Claim 17 containing from 0.1 to 1.05* (w/v « g/ml) of active ingredient. 19> Compositions as claimed in Claim 12 substantially as herein described with reference to Examples 2, 3 or 4. PARTNERS
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL2740667A IL27406A (en) | 1967-02-08 | 1967-02-08 | Stable acid addition salts of bis-(4-hydroxyphenyl)-(quinolyl-2)-methane and their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL2740667A IL27406A (en) | 1967-02-08 | 1967-02-08 | Stable acid addition salts of bis-(4-hydroxyphenyl)-(quinolyl-2)-methane and their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL27406A true IL27406A (en) | 1971-02-25 |
Family
ID=11044111
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL2740667A IL27406A (en) | 1967-02-08 | 1967-02-08 | Stable acid addition salts of bis-(4-hydroxyphenyl)-(quinolyl-2)-methane and their preparation |
Country Status (1)
| Country | Link |
|---|---|
| IL (1) | IL27406A (en) |
-
1967
- 1967-02-08 IL IL2740667A patent/IL27406A/en unknown
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