ES363760A1 - Benzimidazole Derivatives - Google Patents
Benzimidazole DerivativesInfo
- Publication number
- ES363760A1 ES363760A1 ES363760A ES363760A ES363760A1 ES 363760 A1 ES363760 A1 ES 363760A1 ES 363760 A ES363760 A ES 363760A ES 363760 A ES363760 A ES 363760A ES 363760 A1 ES363760 A1 ES 363760A1
- Authority
- ES
- Spain
- Prior art keywords
- compound
- benzimidazole
- reacting
- give
- appropriate
- 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
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 18
- -1 haloaralkyl Chemical group 0.000 abstract 8
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 150000001556 benzimidazoles Chemical class 0.000 abstract 4
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 3
- RAPGMEHFXAWYSY-UHFFFAOYSA-N 6-isothiocyanato-1h-benzimidazole Chemical compound S=C=NC1=CC=C2N=CNC2=C1 RAPGMEHFXAWYSY-UHFFFAOYSA-N 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 2
- 229940125898 compound 5 Drugs 0.000 abstract 2
- 125000005265 dialkylamine group Chemical group 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- 239000012948 isocyanate Substances 0.000 abstract 2
- 238000006396 nitration reaction Methods 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 abstract 1
- RAUWPNXIALNKQM-UHFFFAOYSA-N 4-nitro-1,2-phenylenediamine Chemical compound NC1=CC=C([N+]([O-])=O)C=C1N RAUWPNXIALNKQM-UHFFFAOYSA-N 0.000 abstract 1
- NVKJOXRVEKMMHS-UHFFFAOYSA-N 5-nitro-1,2,4-triazol-3-one Chemical compound [O-][N+](=O)C1=NC(=O)N=N1 NVKJOXRVEKMMHS-UHFFFAOYSA-N 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 150000001266 acyl halides Chemical class 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000005001 aminoaryl group Chemical group 0.000 abstract 1
- 230000000507 anthelmentic effect Effects 0.000 abstract 1
- 229940124339 anthelmintic agent Drugs 0.000 abstract 1
- 239000000921 anthelmintic agent Substances 0.000 abstract 1
- 229940121375 antifungal agent Drugs 0.000 abstract 1
- 239000003429 antifungal agent Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000005111 carboxyalkoxy group Chemical group 0.000 abstract 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 abstract 1
- 125000003106 haloaryl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 150000002540 isothiocyanates Chemical class 0.000 abstract 1
- 229910052751 metal Chemical class 0.000 abstract 1
- 239000002184 metal Chemical class 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical compound O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- E—FIXED CONSTRUCTIONS
- E21—EARTH OR ROCK DRILLING; MINING
- E21D—SHAFTS; TUNNELS; GALLERIES; LARGE UNDERGROUND CHAMBERS
- E21D11/00—Lining tunnels, galleries or other underground cavities, e.g. large underground chambers; Linings therefor; Making such linings in situ, e.g. by assembling
- E21D11/14—Lining predominantly with metal
- E21D11/28—Longitudinal struts, i.e. longitudinal connections between adjoining arches
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Mining & Mineral Resources (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Geology (AREA)
- Structural Engineering (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Geochemistry & Mineralogy (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Civil Engineering (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Architecture (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Novel compounds (I) in which X is O or S R 1 is a five-membered monocyclic heteroaromatic ring containing 1-3 O, S or N atoms R 2 is H, OH, C 1-8 alkyl, C 1-8 alkoxy, aralkyl, acyl, acyloxy, carboxyalkoxy, carbamoyl, N-alkylcarbamoyl, or alkoxycarbonyl R 3 is H, or C 1-8 alkyl and R 4 is H, aralkyl, haloaralkyl, cycloalkyl, C 1-8 alkylamino, di - (C 1-8 alkyl)amino, alkylenimino, hetero - interrupted alkylenimino, cycloalkylamino or a radical R-, RO- or RS- in which R is a C 1-8 univalent aliphatic hydrocarbon, C 1-8 univalent aliphatic halohydrocarbon, aryl, haloaryl, alkaryl, aminoaryl or heterocyclic radical and their acid addition salts and metal complexes when R 2 is H are prepared by: (a) reacting an appropriate 5- NH(R 3 )-substituted benzimidazole with R 4 - C(X)Y where Y is a halogen atom (b) reacting an appropriate 5-RS-CO-N(R 3 )- substituted benzimidazole with a compound ROH to give a compound (I) in which X is O and R 4 is RO (R being radical R from ROH) (c) reacting an appropriate 5-isothiocyanato benzimidazole with a compound ROH or RSH to give a compound (I) in which X is S and R 4 is RO- or RS- (d) reacting a compound (I) in which X is O with phosphorus pentasulphide to give a compound (I) in which X is S (e) reacting an appropriate 5-NH(R 3 )- substituted benzimidazole with an alkyl isocyanate or isothiocyanate to give a compound (I) in which R 4 is alkylamino (f) reacting an appropriate 5-NH(R 3 )- substituted benzimidazole with a dialkylcarbamoyl halide to give a compound (I) in which X is O and R 4 is dialkylamino (g) reacting a compound (I) in which X is O and R 4 is alkylthio with a dialkylamine, alkylenimine or hetero-interrupted alkylenimine to give a compound (I) in which R 4 is dialkylamino, alkylenimino or hetero-interrupted alkylenimino (h) reacting an appropriate 5- isothiocyanato-benzimidazole with a dialkylamine, alkylenimine or hetero-interrupted alkylenimine to give a compound (I) in which X is S and R 4 is dialkylamino, alkylenimino or hetero-interrupted alkylenimino or (i) introducing the group R 2 into an appropriate benzimidazole by reacting an alkali metal salt of a compound (I) in which R 2 is H with an alkyl, aralkyl or acyl halide, or by reacting a compound (I) in which R 2 is H with an alkyl isocyanate to give a compound (I) where R 2 is carbamoyl, or by reacting a compound (I) in which R 2 is H with an alkyl haloformate to give a compound (I) in which R 2 is alkoxycarbonyl followed in any of (a)-(i) by salt formation, where desired. Intermediates isolated are 5-nitro-2-(41-thiazolyl)-benzimidazole, prepared by nitration of the 5 - unsubstituted compound 5 - nitro - 2 - (21 - furyl) - benzimidazole, 5 - nitro - 2 - (21- pyrryl) - benzimidazole and 5 - nitro - 2 - (21- thienyl) - benzimidazole, prepared by reacting the appropriate furan-, pyrrole- or thiophene- 2 - aldehyde with o - amino - p - nitro - aniline 5 - amino - 2 - (41 - thiazolyl) - benzimidazole, prepared by reduction of the 5-nitro compound 5 - isothiocyanato - 2 - (41 - thiazolyl) - benzimidazole, prepared from the 5-phenoxythiocarbonylamino compound by heating in pyridino 5 - nitro - 1 - methoxy - 2 - (41 - thiazolyl)- benzimidazole, prepared by nitration of the 5- unsubstituted compound and 5-amino-1-methoxy - 2 - (41- thiazolyl) - benzimidazole hydrochloride, prepared by reduction of the previous intermediate. Pharmaceutical compositions comprise a novel compound (I) in conjunction with a suitable carrier or diluent and are suitable for oral or parenteral administration as anthelmintics or antifungal agents.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61374667A | 1967-02-03 | 1967-02-03 | |
| US69649668A | 1968-01-09 | 1968-01-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES363760A1 true ES363760A1 (en) | 1970-12-16 |
Family
ID=27087090
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES350083A Expired ES350083A1 (en) | 1967-02-03 | 1968-02-02 | Benzimidazole Derivatives |
| ES363762A Expired ES363762A1 (en) | 1967-02-03 | 1969-02-17 | Benzimidazole Derivatives |
| ES363760A Expired ES363760A1 (en) | 1967-02-03 | 1969-02-17 | Benzimidazole Derivatives |
| ES363761A Expired ES363761A1 (en) | 1967-02-03 | 1969-02-17 | Benzimidazole Derivatives |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES350083A Expired ES350083A1 (en) | 1967-02-03 | 1968-02-02 | Benzimidazole Derivatives |
| ES363762A Expired ES363762A1 (en) | 1967-02-03 | 1969-02-17 | Benzimidazole Derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES363761A Expired ES363761A1 (en) | 1967-02-03 | 1969-02-17 | Benzimidazole Derivatives |
Country Status (19)
| Country | Link |
|---|---|
| AT (5) | AT289828B (en) |
| BE (2) | BE710081A (en) |
| CH (5) | CH545293A (en) |
| CS (1) | CS162651B2 (en) |
| CY (1) | CY653A (en) |
| DE (2) | DE1695545C3 (en) |
| DK (1) | DK139940B (en) |
| ES (4) | ES350083A1 (en) |
| FI (1) | FI52859C (en) |
| FR (1) | FR1580153A (en) |
| GB (2) | GB1198941A (en) |
| IE (1) | IE31812B1 (en) |
| IT (1) | IT1044176B (en) |
| NL (1) | NL157015B (en) |
| NO (1) | NO126484B (en) |
| OA (1) | OA04036A (en) |
| SE (1) | SE346321B (en) |
| SU (1) | SU540569A3 (en) |
| YU (1) | YU33831B (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3711608A (en) * | 1971-04-13 | 1973-01-16 | Merck & Co Inc | The treatment of pain, fever and inflammation with benzimidazoles |
| US3983130A (en) * | 1972-06-02 | 1976-09-28 | E. R. Squibb & Sons, Inc. | Anthelmintic isothiocyanobenzoxazoles |
| US3853894A (en) * | 1972-06-02 | 1974-12-10 | Squibb & Sons Inc | Isothiocyanobenzimidazoles |
| US3985755A (en) * | 1972-06-02 | 1976-10-12 | E. R. Squibb & Sons, Inc. | Pyridine containing isothiocyanobenzoxazoles |
| MA19290A1 (en) * | 1980-05-22 | 1982-04-01 | Ciba Geigy Ag | BENZOLE DERIVATIVES, THEIR PREPARATON AND THEIR THERAPEUTIC USES. |
| SE8604566D0 (en) * | 1986-10-27 | 1986-10-27 | Haessle Ab | NOVEL COMPUNDS |
| EP1581217A4 (en) * | 2002-11-01 | 2007-07-11 | Merck & Co Inc | Carbonylamino-benzimidazole derivatives as androgen receptor modulators |
| CA2540843A1 (en) * | 2003-10-23 | 2005-05-12 | Sterix Limited | Phenyl carboxamide and sulfonamide derivatives for use as 11-beta-hydroxysteroid dehydrogenase |
| GB0324792D0 (en) | 2003-10-23 | 2003-11-26 | Sterix Ltd | Compound |
-
1968
- 1968-01-16 IE IE48/68A patent/IE31812B1/en unknown
- 1968-01-30 BE BE710081D patent/BE710081A/xx not_active IP Right Cessation
- 1968-01-30 FI FI680234A patent/FI52859C/en active
- 1968-01-31 SE SE1277/68A patent/SE346321B/xx unknown
- 1968-02-01 GB GB5259/68A patent/GB1198941A/en not_active Expired
- 1968-02-01 IT IT34575/68A patent/IT1044176B/en active
- 1968-02-01 NL NL6801482.A patent/NL157015B/en not_active IP Right Cessation
- 1968-02-01 GB GB46573/69A patent/GB1198942A/en not_active Expired
- 1968-02-02 CH CH183971A patent/CH545293A/en not_active IP Right Cessation
- 1968-02-02 CH CH184271A patent/CH545796A/xx not_active IP Right Cessation
- 1968-02-02 AT AT545070A patent/AT289828B/en not_active IP Right Cessation
- 1968-02-02 AT AT545170A patent/AT289833B/en not_active IP Right Cessation
- 1968-02-02 ES ES350083A patent/ES350083A1/en not_active Expired
- 1968-02-02 CH CH159768A patent/CH509318A/en not_active IP Right Cessation
- 1968-02-02 NO NO413/68*[A patent/NO126484B/no unknown
- 1968-02-02 AT AT544970A patent/AT289835B/en not_active IP Right Cessation
- 1968-02-02 CH CH184171A patent/CH545295A/en not_active IP Right Cessation
- 1968-02-02 AT AT545270A patent/AT301244B/en not_active IP Right Cessation
- 1968-02-02 CS CS815A patent/CS162651B2/cs unknown
- 1968-02-02 CH CH184071A patent/CH545294A/en not_active IP Right Cessation
- 1968-02-02 DK DK41168AA patent/DK139940B/en not_active IP Right Cessation
- 1968-02-02 FR FR1580153D patent/FR1580153A/fr not_active Expired
- 1968-02-02 DE DE1695545A patent/DE1695545C3/en not_active Expired
- 1968-02-02 AT AT104468A patent/AT293378B/en active
- 1968-02-02 DE DE1795711A patent/DE1795711C3/en not_active Expired
- 1968-02-03 SU SU1215532A patent/SU540569A3/en active
- 1968-02-08 OA OA53178A patent/OA04036A/en unknown
- 1968-08-15 YU YU212/68A patent/YU33831B/en unknown
-
1969
- 1969-02-17 ES ES363762A patent/ES363762A1/en not_active Expired
- 1969-02-17 ES ES363760A patent/ES363760A1/en not_active Expired
- 1969-02-17 ES ES363761A patent/ES363761A1/en not_active Expired
- 1969-06-27 BE BE735281D patent/BE735281A/xx not_active IP Right Cessation
-
1972
- 1972-08-31 CY CY65372A patent/CY653A/en unknown
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