GB1011311A - Antiparasitic compositions and use thereof - Google Patents
Antiparasitic compositions and use thereofInfo
- Publication number
- GB1011311A GB1011311A GB26608/63A GB2660863A GB1011311A GB 1011311 A GB1011311 A GB 1011311A GB 26608/63 A GB26608/63 A GB 26608/63A GB 2660863 A GB2660863 A GB 2660863A GB 1011311 A GB1011311 A GB 1011311A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloro
- hydroxy
- formula
- salt
- phenoxide
- 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
- 239000000203 mixture Substances 0.000 title abstract 3
- 230000002141 anti-parasite Effects 0.000 title 1
- 239000003096 antiparasitic agent Substances 0.000 title 1
- 150000001450 anions Chemical class 0.000 abstract 5
- -1 quinoline compound Chemical class 0.000 abstract 5
- 150000003839 salts Chemical class 0.000 abstract 4
- 239000004480 active ingredient Substances 0.000 abstract 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 3
- KVGOXGQSTGQXDD-UHFFFAOYSA-N 1-decane-sulfonic-acid Chemical compound CCCCCCCCCCS(O)(=O)=O KVGOXGQSTGQXDD-UHFFFAOYSA-N 0.000 abstract 2
- CTTJWXVQRJUJQW-UHFFFAOYSA-N 2,2-dioctyl-3-sulfobutanedioic acid Chemical compound CCCCCCCCC(C(O)=O)(C(C(O)=O)S(O)(=O)=O)CCCCCCCC CTTJWXVQRJUJQW-UHFFFAOYSA-N 0.000 abstract 2
- LHJGJYXLEPZJPM-UHFFFAOYSA-N 2,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1Cl LHJGJYXLEPZJPM-UHFFFAOYSA-N 0.000 abstract 2
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical compound OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 abstract 2
- CNJGWCQEGROXEE-UHFFFAOYSA-M 2-carboxy-4,6-dichlorophenolate Chemical compound OC1=C(Cl)C=C(Cl)C=C1C([O-])=O CNJGWCQEGROXEE-UHFFFAOYSA-M 0.000 abstract 2
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 2
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 abstract 2
- UVGTXNPVQOQFQW-UHFFFAOYSA-N Disophenol Chemical compound OC1=C(I)C=C([N+]([O-])=O)C=C1I UVGTXNPVQOQFQW-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 241001465754 Metazoa Species 0.000 abstract 2
- 229910002651 NO3 Inorganic materials 0.000 abstract 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 abstract 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 abstract 2
- 229940009976 deoxycholate Drugs 0.000 abstract 2
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 abstract 2
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 abstract 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 abstract 2
- FYAQQULBLMNGAH-UHFFFAOYSA-N hexane-1-sulfonic acid Chemical compound CCCCCCS(O)(=O)=O FYAQQULBLMNGAH-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 abstract 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 2
- 229940075930 picrate Drugs 0.000 abstract 2
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 abstract 2
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 abstract 2
- WBWWGRHZICKQGZ-HZAMXZRMSA-N taurocholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)[C@@H](O)C1 WBWWGRHZICKQGZ-HZAMXZRMSA-N 0.000 abstract 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 abstract 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract 1
- RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- CSGQJHQYWJLPKY-UHFFFAOYSA-N CITRAZINIC ACID Chemical compound OC(=O)C=1C=C(O)NC(=O)C=1 CSGQJHQYWJLPKY-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- XGDCECUDODFNRZ-UHFFFAOYSA-N OC=1C=C(C(=O)O)C=C(N1)O.ClC1=CC=C2C(=C(C=NC2=C1)C(=O)O)O Chemical compound OC=1C=C(C(=O)O)C=C(N1)O.ClC1=CC=C2C(=C(C=NC2=C1)C(=O)O)O XGDCECUDODFNRZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002202 Polyethylene glycol Substances 0.000 abstract 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 abstract 1
- 159000000021 acetate salts Chemical class 0.000 abstract 1
- 239000011149 active material Substances 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 1
- 230000000507 anthelmentic effect Effects 0.000 abstract 1
- 230000000398 anti-amebic effect Effects 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 230000001572 anti-trichomonad Effects 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 239000007900 aqueous suspension Substances 0.000 abstract 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 229920001429 chelating resin Polymers 0.000 abstract 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000796 flavoring agent Substances 0.000 abstract 1
- 235000013355 food flavoring agent Nutrition 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 239000003456 ion exchange resin Substances 0.000 abstract 1
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 1
- 238000005649 metathesis reaction Methods 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 229920001223 polyethylene glycol Polymers 0.000 abstract 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 1
- 239000003755 preservative agent Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 229940035048 sorbitan monostearate Drugs 0.000 abstract 1
- 235000011076 sorbitan monostearate Nutrition 0.000 abstract 1
- 239000001587 sorbitan monostearate Substances 0.000 abstract 1
- 239000000375 suspending agent Substances 0.000 abstract 1
- 235000015112 vegetable and seed oil Nutrition 0.000 abstract 1
- 239000008158 vegetable oil Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/475—Quinolines; Isoquinolines having an indole ring, e.g. yohimbine, reserpine, strychnine, vinblastine
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Imidazo - [1,2-a : 3,4-a1] - diquinolin - 15 -ium salts of formula <FORM:1011311/C2/1> where R and R1 are hydrogen or methyl and X is a physiologically acceptable anion are prepared by condensing a quinoline compound of formula <FORM:1011311/C2/2> with a quinaldine of formula <FORM:1011311/C2/3> where R and R1 are as above, in the presence of an inert organic solvent containing iodine. The resulting iodide may be converted to any desired salt by treating an aqueous or aqueous alcoholic solution of the iode with a strong base ion exchange resin in the hydroxyl form (e.g. that sold under the Trade Mark Amberlite IRA-410) and treating the hydroxide directly with the acid. Alternatively, the acetate salt is formed from the hydroxide and the desired salt formed by metathesis using the sodium or potassium salt of an acid having the desired anion. Specified anions are the chloride, bromide, iodide, nitrate, bisulphite, hemisulphate, perchlorate, acetate, palmitate, stearate, hemipamoate, picrate, 1-decanesulphonate, 4-chloro - 2 - (5 - chlorosalicyl) phenoxide, 3-hydroxy - 2 - naphthoate, dodecylsulphate, cyclohexanesulphamate, 2,4,5 - trichlorophenoxide, 2,21 - thiobis - (4,6 - dichlorophenoxide), deoxycholate, 7 - chloro - 4 - hydroxy - 3 - quinolinecarboxylate 2,6 - dihydroxyisonicotinate, 1 - bromo - 2 - naphthoxide, hemiadipate, p-toluenesulphonate, hemi - (5,51 - thiodisalicylate), 3,5 - dichlorosalicylate, taurocholate, dioctylsulphosuccinate, 2,6 - di - iodo - 4 - nitrophenoxide, 1 - hexanesulphonate, 4 - chlorobenzenesulphonate, decanoate and phenolphthaleinate.ALSO:An anthelmintic composition also having antibacterial, antiamebic and antitrichomonal activity, in dosage unit form, comprises, as active ingredient, imidazo [1, 2-a : 3, 4-a1] diquinolin-15-ium salt having the formula <FORM:1011311/A5-A6/1> wherein R and R1 each independently represent hydrogen or methyl and X is a physiologically acceptable anion. Specified anions are the chloride, bromide, iodide, nitrate, bisulphite, hemisulphate, perchlorate, acetate, palmitate, stearate, hemipamoate, picrate, 1-decanesulphonate, 4-chloro-2-(5-chlorosalicyl) phenoxide, 3-hydroxy, 2-naphthoate, dodecylsulphate, cyclohexanesulphamate, 2, 4, 5-trichloro-phenoxide, 2, 21-thiobis (4, 6-dichlorophenoxide), deoxycholate, 7-chloro-4-hydroxy -3-quinolinecarboxlate, 2, 6-dihydroxyisonicotinate, 1-bromo-2-naphthoxide, hemiadipate, p-toluenesulphonate, hemi-(5, 51-thiodisalicylate), 3, 5-dichlorosalicylate, taurocholate, dioctylsulphosuccinate, 2, 6-di-iodo-4-nitrophenoxide, 1-hexanesulphonate, H-chlorobenzene sulphonate, decanoate and phenolphthaleinate. The composition may be used orally e.g. in the form of an aqueous suspension or solution containing suspending agents or solubilizers, preservatives and flavouring agents; or in the form of tablets or capsules in which the active ingredient is dissolved in a vegetable oil. The active ingredient may be dissolved in water containing sorbitan monostearate and polyethylene glycol. In the case of animals, the active material may be mixed with the animal feed.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB26608/63A GB1011311A (en) | 1963-07-04 | 1963-07-04 | Antiparasitic compositions and use thereof |
| US375638A US3253986A (en) | 1963-07-04 | 1964-06-16 | Antiparasitic compositions and use thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB26608/63A GB1011311A (en) | 1963-07-04 | 1963-07-04 | Antiparasitic compositions and use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1011311A true GB1011311A (en) | 1965-11-24 |
Family
ID=10246299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB26608/63A Expired GB1011311A (en) | 1963-07-04 | 1963-07-04 | Antiparasitic compositions and use thereof |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3253986A (en) |
| GB (1) | GB1011311A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB988483A (en) * | 1963-02-11 | 1965-04-07 | Soc D Etudes Prod Chimique | Quinoline derivative and preparation thereof |
| US3541100A (en) * | 1967-12-14 | 1970-11-17 | American Cyanamid Co | Benzheteroazolo(2,3-a)isoquinolium salts |
| GB1278272A (en) * | 1969-02-19 | 1972-06-21 | Pfizer Ltd | Substituted hexahydro-imidazoquinolines |
| US4207320A (en) * | 1978-08-28 | 1980-06-10 | Warner-Lambert Company | Amino-substituted imidazo[1,2-a:3,4-a']diquinolin-15-ium salts compositions and method of use |
| CA2644613A1 (en) * | 2006-03-07 | 2007-09-13 | Endacea, Inc. | Compositions and methods for treating respiratory disorders |
| JP5558875B2 (en) * | 2009-03-19 | 2014-07-23 | 日本曹達株式会社 | Novel inclusion complex, epoxy resin composition and epoxy resin composition for semiconductor encapsulation |
-
1963
- 1963-07-04 GB GB26608/63A patent/GB1011311A/en not_active Expired
-
1964
- 1964-06-16 US US375638A patent/US3253986A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US3253986A (en) | 1966-05-31 |
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