CS198195B2 - Process for preparing 4-imino-1,3-diazabicyclo/3,1,0/hexan-2-one - Google Patents
Process for preparing 4-imino-1,3-diazabicyclo/3,1,0/hexan-2-one Download PDFInfo
- Publication number
- CS198195B2 CS198195B2 CS764432A CS443276A CS198195B2 CS 198195 B2 CS198195 B2 CS 198195B2 CS 764432 A CS764432 A CS 764432A CS 443276 A CS443276 A CS 443276A CS 198195 B2 CS198195 B2 CS 198195B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- hexan
- imino
- diazabicyclo
- july
- compound
- Prior art date
Links
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 title description 8
- 238000004519 manufacturing process Methods 0.000 title 1
- BIXBBIPTYBJTRY-UHFFFAOYSA-N imexon Chemical compound NC1=NC(=O)N2CC12 BIXBBIPTYBJTRY-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 9
- 150000003839 salts Chemical class 0.000 abstract description 4
- 230000003327 cancerostatic effect Effects 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 239000002253 acid Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 238000006317 isomerization reaction Methods 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 241000700159 Rattus Species 0.000 description 9
- 238000001990 intravenous administration Methods 0.000 description 9
- 206010028980 Neoplasm Diseases 0.000 description 6
- 230000037396 body weight Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 210000003743 erythrocyte Anatomy 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 210000000265 leukocyte Anatomy 0.000 description 4
- 239000002504 physiological saline solution Substances 0.000 description 4
- 210000000952 spleen Anatomy 0.000 description 4
- 238000012453 sprague-dawley rat model Methods 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000007123 defense Effects 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 230000003308 immunostimulating effect Effects 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- -1 4-amino-1,3-diazabicyclo [3.1.0] hexan-2-one Chemical compound 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- 206010039491 Sarcoma Diseases 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 210000001367 artery Anatomy 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 230000003993 interaction Effects 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
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- ZMXDDKWLCZADIW-WFVSFCRTSA-N 1-deuterio-n,n-dimethylformamide Chemical compound [2H]C(=O)N(C)C ZMXDDKWLCZADIW-WFVSFCRTSA-N 0.000 description 1
- 229920001817 Agar Polymers 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
- 208000035143 Bacterial infection Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000206672 Gelidium Species 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
- 229930195725 Mannitol Natural products 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000001363 autoimmune Effects 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 229960004397 cyclophosphamide Drugs 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004698 lymphocyte Anatomy 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
- 230000004060 metabolic process Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 238000004452 microanalysis Methods 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
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000004989 spleen cell Anatomy 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000009747 swallowing Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 210000001519 tissue Anatomy 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
- 230000004614 tumor growth Effects 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Color Printing (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752530398 DE2530398A1 (de) | 1975-07-08 | 1975-07-08 | Organische verbindung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS198195B2 true CS198195B2 (en) | 1980-05-30 |
Family
ID=5950951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS764432A CS198195B2 (en) | 1975-07-08 | 1976-07-05 | Process for preparing 4-imino-1,3-diazabicyclo/3,1,0/hexan-2-one |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4083987A (en, 2012) |
| JP (1) | JPS5210290A (en, 2012) |
| AR (1) | AR208802A1 (en, 2012) |
| AT (1) | AT345846B (en, 2012) |
| AU (1) | AU497292B2 (en, 2012) |
| BE (1) | BE843803A (en, 2012) |
| CA (1) | CA1069125A (en, 2012) |
| CH (1) | CH598259A5 (en, 2012) |
| CS (1) | CS198195B2 (en, 2012) |
| DD (1) | DD125079A5 (en, 2012) |
| DE (1) | DE2530398A1 (en, 2012) |
| DK (1) | DK139752C (en, 2012) |
| ES (1) | ES449597A1 (en, 2012) |
| FI (1) | FI59250C (en, 2012) |
| FR (1) | FR2316945A1 (en, 2012) |
| GB (1) | GB1490486A (en, 2012) |
| HU (1) | HU170252B (en, 2012) |
| IL (1) | IL49964A (en, 2012) |
| IN (1) | IN146367B (en, 2012) |
| LU (1) | LU75314A1 (en, 2012) |
| NL (1) | NL160564C (en, 2012) |
| PL (1) | PL98937B1 (en, 2012) |
| PT (1) | PT65327B (en, 2012) |
| SE (1) | SE409864B (en, 2012) |
| SU (1) | SU604482A3 (en, 2012) |
| ZA (1) | ZA763977B (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5369119A (en) * | 1988-07-28 | 1994-11-29 | Boehringer Mannheim Gmbh | Use of imexon as an immune suppressive and pharmaceutical compositions containing imexon |
| DE3844655A1 (de) * | 1988-07-28 | 1990-05-17 | Boehringer Mannheim Gmbh | Verwendung von imexon als immunsuppressivum |
| DE3825667A1 (de) * | 1988-07-28 | 1990-03-15 | Boehringer Mannheim Gmbh | Verwendung von imexon als immunsuppressivum |
| DE3841879A1 (de) * | 1988-12-13 | 1990-06-21 | Boehringer Mannheim Gmbh | Neue imidazolidin-derivate, verfahren zu ihrer herstellung sowie arzneimittel, die diese verbindungen enthalten |
| US20030129222A1 (en) * | 2000-11-21 | 2003-07-10 | Gabriel Lopez-Berestein | Liposomal imexon |
| WO2002041871A2 (en) * | 2000-11-21 | 2002-05-30 | Board Of Regents, The University Of Texas System | Composition comprising an imexon or derivatives thereof and lipids |
| US6476236B1 (en) | 2001-11-26 | 2002-11-05 | The Arizona Board Of Regents | Synthesis of 2-cyanoaziridine-1-carboxamide |
| US20080096947A1 (en) * | 2004-10-15 | 2008-04-24 | Heidelberg Pharma Ag | Parenteral Forms Of Administration Of Imexon And Method For The Production Thereof |
| WO2008045686A2 (en) * | 2006-10-12 | 2008-04-17 | The Arizona Board Of Regents On Behalf Of The University Of Arizona | Enantiomerically enriched iminopyrrolidone azirdine compositions |
-
1975
- 1975-07-08 DE DE19752530398 patent/DE2530398A1/de not_active Withdrawn
-
1976
- 1976-05-26 US US05/690,340 patent/US4083987A/en not_active Expired - Lifetime
- 1976-06-28 CA CA255,790A patent/CA1069125A/en not_active Expired
- 1976-06-29 DD DD193619A patent/DD125079A5/xx unknown
- 1976-07-01 DK DK297176A patent/DK139752C/da active
- 1976-07-02 GB GB27657/76A patent/GB1490486A/en not_active Expired
- 1976-07-02 AR AR263845A patent/AR208802A1/es active
- 1976-07-02 IL IL49964A patent/IL49964A/en unknown
- 1976-07-05 AU AU15596/76A patent/AU497292B2/en not_active Expired
- 1976-07-05 FI FI761958A patent/FI59250C/fi not_active IP Right Cessation
- 1976-07-05 CH CH859076A patent/CH598259A5/xx not_active IP Right Cessation
- 1976-07-05 ZA ZA763977A patent/ZA763977B/xx unknown
- 1976-07-05 CS CS764432A patent/CS198195B2/cs unknown
- 1976-07-05 BE BE168650A patent/BE843803A/xx unknown
- 1976-07-05 SE SE7607675A patent/SE409864B/xx unknown
- 1976-07-05 HU HUBO1622A patent/HU170252B/hu unknown
- 1976-07-06 NL NL7607429.A patent/NL160564C/xx not_active IP Right Cessation
- 1976-07-06 LU LU75314A patent/LU75314A1/xx unknown
- 1976-07-06 AT AT493176A patent/AT345846B/de not_active IP Right Cessation
- 1976-07-06 ES ES449597A patent/ES449597A1/es not_active Expired
- 1976-07-07 PT PT65327A patent/PT65327B/pt unknown
- 1976-07-07 PL PL1976190969A patent/PL98937B1/pl unknown
- 1976-07-07 FR FR7620739A patent/FR2316945A1/fr active Granted
- 1976-07-08 SU SU762379563A patent/SU604482A3/ru active
- 1976-07-08 JP JP51081456A patent/JPS5210290A/ja active Granted
-
1977
- 1977-07-01 IN IN992/CAL/77A patent/IN146367B/en unknown
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