SU883002A1 - Производные антрахинона, обладающие противоамебной активностью в отношении еNтамIева нISтоLIтIса - Google Patents
Производные антрахинона, обладающие противоамебной активностью в отношении еNтамIева нISтоLIтIса Download PDFInfo
- Publication number
- SU883002A1 SU883002A1 SU762389053A SU2389053A SU883002A1 SU 883002 A1 SU883002 A1 SU 883002A1 SU 762389053 A SU762389053 A SU 762389053A SU 2389053 A SU2389053 A SU 2389053A SU 883002 A1 SU883002 A1 SU 883002A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- entamieba
- histolitica
- antiamebic
- activity towards
- anthraquinone derivatives
- Prior art date
Links
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 title claims description 3
- 150000004056 anthraquinones Chemical class 0.000 title claims description 3
- 230000000398 anti-amebic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 9
- 206010001981 Amoebic infections Diseases 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 7
- 150000001409 amidines Chemical class 0.000 abstract 2
- 206010061217 Infestation Diseases 0.000 abstract 1
- 229940124343 antiamebic agent Drugs 0.000 abstract 1
- 239000000059 antiamebic agent Substances 0.000 abstract 1
- 230000002440 hepatic effect Effects 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 241000700159 Rattus Species 0.000 description 8
- 208000015181 infectious disease Diseases 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000013078 crystal Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 241000699800 Cricetinae Species 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 210000004185 liver Anatomy 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 241000224421 Heterolobosea Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 210000003001 amoeba Anatomy 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 208000006454 hepatitis Diseases 0.000 description 2
- 231100000283 hepatitis Toxicity 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
- 239000002609 medium Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 210000000664 rectum Anatomy 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- WQOWBWVMZPPPGX-UHFFFAOYSA-N 2,6-diaminoanthracene-9,10-dione Chemical compound NC1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 WQOWBWVMZPPPGX-UHFFFAOYSA-N 0.000 description 1
- FARSXMMESQDZMY-UHFFFAOYSA-N 4-chloro-n,n-dimethylbenzamide Chemical compound CN(C)C(=O)C1=CC=C(Cl)C=C1 FARSXMMESQDZMY-UHFFFAOYSA-N 0.000 description 1
- LIPBGDOQGGYIKB-UHFFFAOYSA-N 4-chloro-n,n-dimethylbenzenecarboximidamide Chemical compound CN(C)C(=N)C1=CC=C(Cl)C=C1 LIPBGDOQGGYIKB-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose 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](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 241000224489 Amoeba Species 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 241000894006 Bacteria Species 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-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
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 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 1
- 241000699673 Mesocricetus auratus Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N 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
- 229930006000 Sucrose Natural products 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000004534 cecum Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000002550 fecal effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012737 fresh medium Substances 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- KYJXFJJPTBJREV-UHFFFAOYSA-N n,n-dimethylcyclobutanecarboxamide Chemical compound CN(C)C(=O)C1CCC1 KYJXFJJPTBJREV-UHFFFAOYSA-N 0.000 description 1
- NMXQUMZGXPVJBQ-UHFFFAOYSA-N n,n-dimethylcyclopropanecarboximidamide Chemical compound CN(C)C(=N)C1CC1 NMXQUMZGXPVJBQ-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/195—Radicals derived from nitrogen analogues of carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D223/12—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60680575A | 1975-08-22 | 1975-08-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU883002A1 true SU883002A1 (ru) | 1981-11-23 |
Family
ID=24429543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762389053A SU883002A1 (ru) | 1975-08-22 | 1976-08-19 | Производные антрахинона, обладающие противоамебной активностью в отношении еNтамIева нISтоLIтIса |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5225763A (cg-RX-API-DMAC7.html) |
| AR (1) | AR213625A1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU508586B2 (cg-RX-API-DMAC7.html) |
| BE (1) | BE845369A (cg-RX-API-DMAC7.html) |
| CA (1) | CA1098127A (cg-RX-API-DMAC7.html) |
| CS (1) | CS212773B2 (cg-RX-API-DMAC7.html) |
| DE (1) | DE2637544A1 (cg-RX-API-DMAC7.html) |
| EG (1) | EG12401A (cg-RX-API-DMAC7.html) |
| ES (1) | ES450859A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2321281A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1553600A (cg-RX-API-DMAC7.html) |
| GR (1) | GR60420B (cg-RX-API-DMAC7.html) |
| HU (1) | HU173298B (cg-RX-API-DMAC7.html) |
| LU (1) | LU75636A1 (cg-RX-API-DMAC7.html) |
| NL (1) | NL7609230A (cg-RX-API-DMAC7.html) |
| NZ (1) | NZ181596A (cg-RX-API-DMAC7.html) |
| PH (1) | PH13216A (cg-RX-API-DMAC7.html) |
| PL (1) | PL191945A1 (cg-RX-API-DMAC7.html) |
| PT (1) | PT65506B (cg-RX-API-DMAC7.html) |
| SU (1) | SU883002A1 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA764516B (cg-RX-API-DMAC7.html) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1154489B (de) * | 1961-05-05 | 1963-09-19 | Basf Ag | Verfahren zur Trennung von Mono- und Diaminoanthrachinonen |
-
1976
- 1976-07-27 ZA ZA764516A patent/ZA764516B/xx unknown
- 1976-07-30 PH PH18739A patent/PH13216A/en unknown
- 1976-08-03 GB GB31334/76A patent/GB1553600A/en not_active Expired
- 1976-08-05 NZ NZ181596A patent/NZ181596A/xx unknown
- 1976-08-06 GR GR51428A patent/GR60420B/el unknown
- 1976-08-06 AR AR264245A patent/AR213625A1/es active
- 1976-08-09 AU AU16693/76A patent/AU508586B2/en not_active Expired
- 1976-08-12 CA CA257,701A patent/CA1098127A/en not_active Expired
- 1976-08-14 EG EG498/76A patent/EG12401A/xx active
- 1976-08-18 HU HU76AE473A patent/HU173298B/hu unknown
- 1976-08-19 FR FR7625243A patent/FR2321281A1/fr active Granted
- 1976-08-19 NL NL7609230A patent/NL7609230A/xx not_active Application Discontinuation
- 1976-08-19 SU SU762389053A patent/SU883002A1/ru active
- 1976-08-20 CS CS765425A patent/CS212773B2/cs unknown
- 1976-08-20 ES ES450859A patent/ES450859A1/es not_active Expired
- 1976-08-20 PT PT65506A patent/PT65506B/pt unknown
- 1976-08-20 BE BE169950A patent/BE845369A/xx not_active IP Right Cessation
- 1976-08-20 DE DE19762637544 patent/DE2637544A1/de not_active Withdrawn
- 1976-08-20 LU LU75636A patent/LU75636A1/xx unknown
- 1976-08-21 PL PL19194576A patent/PL191945A1/xx unknown
- 1976-08-23 JP JP51099760A patent/JPS5225763A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL7609230A (nl) | 1977-02-24 |
| EG12401A (en) | 1980-03-31 |
| JPS5225763A (en) | 1977-02-25 |
| AR213625A1 (es) | 1979-02-28 |
| CA1098127A (en) | 1981-03-24 |
| DE2637544A1 (de) | 1977-03-03 |
| FR2321281A1 (fr) | 1977-03-18 |
| NZ181596A (en) | 1978-12-18 |
| CS212773B2 (en) | 1982-03-26 |
| PT65506B (en) | 1978-02-15 |
| GR60420B (en) | 1978-05-25 |
| BE845369A (fr) | 1977-02-21 |
| PL191945A1 (pl) | 1978-12-04 |
| AU1669376A (en) | 1978-02-16 |
| PT65506A (en) | 1976-09-01 |
| PH13216A (en) | 1980-02-07 |
| ES450859A1 (es) | 1978-04-01 |
| LU75636A1 (cg-RX-API-DMAC7.html) | 1977-03-29 |
| GB1553600A (en) | 1979-09-26 |
| AU508586B2 (en) | 1980-03-27 |
| ZA764516B (en) | 1977-07-27 |
| FR2321281B1 (cg-RX-API-DMAC7.html) | 1979-07-27 |
| HU173298B (hu) | 1979-04-28 |
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