GB1310998A - 4,5,6,7-tetrahydrobenzimidazoles - Google Patents
4,5,6,7-tetrahydrobenzimidazolesInfo
- Publication number
- GB1310998A GB1310998A GB4385070A GB4385070A GB1310998A GB 1310998 A GB1310998 A GB 1310998A GB 4385070 A GB4385070 A GB 4385070A GB 4385070 A GB4385070 A GB 4385070A GB 1310998 A GB1310998 A GB 1310998A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- carbon atoms
- radical
- alkyl group
- group containing
- 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
- KAWYASGZISVRAL-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1h-benzimidazole Chemical class C1CCCC2=C1N=CN2 KAWYASGZISVRAL-UHFFFAOYSA-N 0.000 title abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 17
- 125000000217 alkyl group Chemical group 0.000 abstract 15
- -1 4-piperidyl radical Chemical class 0.000 abstract 13
- 150000003254 radicals Chemical class 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract 2
- 239000012458 free base Substances 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 abstract 1
- OJHWPOJTJKJBLA-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-benzimidazole Chemical class C1C=CC=C2NCNC21 OJHWPOJTJKJBLA-UHFFFAOYSA-N 0.000 abstract 1
- DBCZFJFZKAQGSL-UHFFFAOYSA-N 2,3-diacetyloxypropanoic acid Chemical compound CC(=O)OCC(C(O)=O)OC(C)=O DBCZFJFZKAQGSL-UHFFFAOYSA-N 0.000 abstract 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 abstract 1
- 239000002168 alkylating agent Substances 0.000 abstract 1
- 229940100198 alkylating agent Drugs 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000000089 arabinosyl group Chemical group C1([C@@H](O)[C@H](O)[C@H](O)CO1)* 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 abstract 1
- 150000002402 hexoses Chemical class 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- QZIQJVCYUQZDIR-UHFFFAOYSA-N mechlorethamine hydrochloride Chemical compound Cl.ClCCN(C)CCCl QZIQJVCYUQZDIR-UHFFFAOYSA-N 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 150000002972 pentoses Chemical class 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 229910052703 rhodium Inorganic materials 0.000 abstract 1
- 239000010948 rhodium Substances 0.000 abstract 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 abstract 1
- 125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 abstract 1
- 150000003538 tetroses Chemical class 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- 125000000969 xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/10—Radicals substituted by halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/16—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/20—Two benzimidazolyl-2 radicals linked together directly or via a hydrocarbon or substituted hydrocarbon radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
- C10M2215/222—Triazines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/223—Five-membered rings containing nitrogen and carbon only
- C10M2215/224—Imidazoles
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
- C10M2219/024—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of esters, e.g. fats
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1310998 Tetrahydrobenzimidazoles PLIVA PHARMACEUTICAL & CHEMICAL WORKS 14 Sept 1970 [26 Sept 1969] 43850/70 Heading C2C [Also in Divisions C3 and C5] Novel 4,5,6,7 - tetrahydrobenzimidazoles of the formula in which R 1 represents a hydrogen atom, a straight or branched alkyl group containing 1 to 18 carbon atoms, a hydroxyalkyl or carboxyalkyl group containing 1 to 4 carbon atoms in the alkyl group, a 5 or 6 membered cycloalkyl, alkylcycloalkyl or cycloalkylalkyl group, an arylalkyl group containing 1 to 4 carbon atoms in the alkyl group, a glucosyl, arabinosyl, xylosyl or ribosyl group or other sugar residue derived from hexoses, pentoses or tetroses, or R 1 is the group A-Z, in which A is a straight or branched alkylene group containing 1 to 4 carbon atoms and Z is an amino, lower monoalkylamino, lower dialkylamino, morpholino, N-pyrrolidino, N-piperidino, N-piperazino, N<SP>1</SP>-lower alkyl-N-piperazino, N<SP>1</SP>- (# - hydroxy - lower alkyl) - N - piperazino or N<SP>1</SP> - (# - hydroxy - alkoxy - lower alkyl) - N- piperazino group, R 2 represents a hydrogen atom, a straight or branched alkyl group containing 1 to 20 carbon atoms, a trifluoromethyl, hydroxymethyl or carboxyl group, a carboxyalkyl group containing 1 to 4 carbon atoms, a phenyl-lower alkyl or cyclohexyl-lower alkyl group, a dialkylaminoethylaminocarbonylalkyl, dialkylaminoethylaminocarbonyl or dialkylaminoethoxycarbonylalkyl group containing 1 to 4 carbon atoms in the alkyl group, the 3-(2,3- dihydroxy propionic acid) group, the 3-(2,3- diacetoxy propionic acid methyl ester) group or the 3 - (2,3 - diacetoxy propionic acid dialkylaminoethylamide) group containing 1 to 4 carbon atoms in the alkyl group, the 5-(2,3,4,5- tetrahydroxy valeric acid) group, a polyhydroxyalkyl group containing 4 to 6 carbon atoms, a cyclopentyl or cyclohexyl radical, an alkylcyclohexyl radical containing 1 to 4 carbon atoms in the alkyl group, the carboxyoyclohexyl radical, the 2-, 3- or 4-piperidyl radical, a phenyl, mono or dialkylphenyl radical containing 1 to 4 carbon atoms in the alkyl group, a mono- or dialkoxy phenyl, mono- or dialkoxybenzyl or mono- or dialkoxyphenylethyl radical containing 1 to 4 carbon atoms in the alkoxy group, a 3,4-methylene dioxyphenyl, 3,4-methylene dioxybenzyl or 3,4-methylene dioxyphenylethyl radical, a tetrahydrofuryl group, an acylaminophenyl radical in which the acyl groups are derived from an aliphatic carboxylic acid containing 1 to 3 carbon atoms, the fluorophenyl radical, the 4,5,6,7-tetrahydrobenzimidazolyl - (2) - 1,2 - dihydroxyethyl or 4,5,6,7 - tetrahydrobenzimidazolyl - (2) - 1,2,3,4- tetrahydroxybutyl radical, an imidazolylalkyl, triazolylalkyl or tetrazolylalkyl group containing 1 to 4 carbon atoms in the alkyl group, R 3 represents a hydrogen atom, a straight or branched alkyl group containing 1 to 18 carbon atoms, a carboxyl group or an alkoxycarbonyl radical containing 1 to 4 carbon atoms in the alkoxy group, and R 4 represents a hydrogen atom, or a straight or branched alkyl group containing 1 to 4 carbon atoms, and the acid addition salts and quaternary ammonium salts of the compounds of Formula I above, excepting specifically 4, 5, 6, 7-tetrahydrobenzimidazole and 2-methyl, 5-methyl, 1,2-dimethyl, 2,5- dimethyl, 2-ethyl, 2-ethyl-5-methyl, 2-n-propyl, 2-n-propyl-5-methyl, 2-isopropyl, 2-isobutyl, 2- hexyl, 2-cyolohexyl, 2-phenyl and 2-amisyl- 4,5,6,7-tetrahydrobenzimidazoles, are prepared by hydrogenating a benzimidazole of formula where R 1 , R 2 , R 3 and R 4 are as above, or the unsaturated precursors thereof which can be hydrogenated, (a) in the form of acid addition salts or (b) in the form of free bases and in the presence of at least one equivalent of an acid for each basic group, in the presence of rhodium catalysts, and a polar solvent and, if required, the salt of the 4,5,6,7-tetrahydrobenzimidazole obtained is converted into the free base in known manner and, if required, the free base is converted into an acid addition salt or quaternary ammonium salt by reaction with an inorganic or organic acid or alkylating agent.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691948795 DE1948795A1 (en) | 1969-09-26 | 1969-09-26 | 4,5,6,7-Tetrahydrobenzimidazoles, process for their preparation and their use as corrosion inhibitors and anti-aging agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1310998A true GB1310998A (en) | 1973-03-21 |
Family
ID=5746643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4385070A Expired GB1310998A (en) | 1969-09-26 | 1970-09-14 | 4,5,6,7-tetrahydrobenzimidazoles |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS4924072B1 (en) |
| DE (1) | DE1948795A1 (en) |
| FR (1) | FR2062636A5 (en) |
| GB (1) | GB1310998A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015086513A1 (en) * | 2013-12-09 | 2015-06-18 | Ucb Biopharma Sprl | Tetrahydrobenzimidazole derivatives as modulators of tnf activity |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR69291B (en) * | 1979-06-25 | 1982-05-13 | May & Baker Ltd | |
| DE2948056A1 (en) * | 1979-11-29 | 1981-06-04 | Boehringer Mannheim Gmbh, 6800 Mannheim | NEW AMINOPROPANOL DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS |
| CA2004911A1 (en) * | 1988-12-22 | 1990-06-22 | Mitsuaki Ohta | 4,5,6,7-tetrahydrobenzimidazole derivatives |
| US6437147B1 (en) | 2000-03-17 | 2002-08-20 | Novo Nordisk | Imidazole compounds |
| US10696558B2 (en) * | 2017-03-21 | 2020-06-30 | Exxonmobil Research & Engineering Company | Zeolitic imidazolate framework materials, their synthesis and use |
-
1969
- 1969-09-26 DE DE19691948795 patent/DE1948795A1/en active Pending
-
1970
- 1970-09-14 GB GB4385070A patent/GB1310998A/en not_active Expired
- 1970-09-24 JP JP8305970A patent/JPS4924072B1/ja active Pending
- 1970-09-25 FR FR7034761A patent/FR2062636A5/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015086513A1 (en) * | 2013-12-09 | 2015-06-18 | Ucb Biopharma Sprl | Tetrahydrobenzimidazole derivatives as modulators of tnf activity |
| US10093652B2 (en) | 2013-12-09 | 2018-10-09 | Ucb Biopharma Sprl | Tetrahydrobenzimidazole derivatives as modulators of TNF activity |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4924072B1 (en) | 1974-06-20 |
| DE1948795A1 (en) | 1971-04-08 |
| FR2062636A5 (en) | 1971-06-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |