GB1263561A - New sulphanilamide derivatives, their production and compositions containing same - Google Patents
New sulphanilamide derivatives, their production and compositions containing sameInfo
- Publication number
- GB1263561A GB1263561A GB03513/69A GB1351369A GB1263561A GB 1263561 A GB1263561 A GB 1263561A GB 03513/69 A GB03513/69 A GB 03513/69A GB 1351369 A GB1351369 A GB 1351369A GB 1263561 A GB1263561 A GB 1263561A
- Authority
- GB
- United Kingdom
- Prior art keywords
- butyl
- tert
- diamine
- compounds
- propionamide
- 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 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 5
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 abstract 2
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 2
- JEQDSBVHLKBEIZ-REOHCLBHSA-N (2s)-2-chloropropanoyl chloride Chemical compound C[C@H](Cl)C(Cl)=O JEQDSBVHLKBEIZ-REOHCLBHSA-N 0.000 abstract 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 1
- FCFRBBZLZPIINI-UHFFFAOYSA-N 2-(benzylamino)-n-butylpropanamide Chemical compound CCCCNC(=O)C(C)NCC1=CC=CC=C1 FCFRBBZLZPIINI-UHFFFAOYSA-N 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- SMSDMJOVJVHWIU-UHFFFAOYSA-N N-butyl-2-chlorobutanamide Chemical compound C(CCC)NC(C(CC)Cl)=O SMSDMJOVJVHWIU-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- -1 alkaline earth metal salt Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical class OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000002218 hypoglycaemic effect Effects 0.000 abstract 1
- 150000002461 imidazolidines Chemical class 0.000 abstract 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 230000009467 reduction Effects 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
- 238000006894 reductive elimination reaction Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000010561 standard procedure Methods 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 125000005039 triarylmethyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/22—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
- C07D203/24—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/46—Nitrogen atoms not forming part of a nitro radical with only hydrogen atoms attached to said nitrogen 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
- C07D235/24—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
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,263,561. Imidazolidine derivatives. J. R. GEIGY A.G. 14 March, 1969 [14 March, 1968 (2)], No. 13513/69. Heading C2C. Novel Compounds I (including salts thereof) wherein R 1 signifies alkyl or alkenyl of at most 5 carbons or an optionally alkyl-substituted cycloalkyl or cycloalkenyl group or a cycloalkyl-alkyl or cycloalkenyl-alkyl group of at most 7 carbons and R 2 is Me or Et, are obtained: (a) by reacting a Compound II (R 3 signifies H, Me, allyl, aryldiaryl- or triarylmethyl and X signifies NH 2 or a group which can be converted into NH 2 by hydrolysis, reduction or reductive cleavage) with a reactive cyanic acid derivative; (b) by reacting a Compound III with a nitrile, R 1 NH.CN or with an alkali or alkaline earth metal salt thereof; (c) by reducing a Compound V (R 1 <SP>1</SP> signifies C 3-5 alkenyl or C 5-7 cycloalkenyl); or (d) by reacting a functional derivative of a sulphonic acid VI with an imidazoline VII (also described as the hydrobromide) Compounds II, III and VII are in general prepared by standard methods. Intermediates to Compounds I, e.g. compounds wherein in place of NH 2 in I there is an MeCONH- group may be produced by methods (a) to (d). N - Tert. butyl - (2 - benzylamino) - propionamide (also described as the hydrochloride), obtained by the interaction of benzylamine and N - tert. - butyl - 2 - chloro - propionamide, reacts with lithium aluminium hydride to afford N<SP>1</SP>- tert.-butyl-N<SP>2</SP>-benzyl-1,2-propane-diamine; the diamine is debenzylated to give N<SP>1</SP>-tert.-butyl- 1,2 - propane - diamine dihydrobromide. The following related compounds are also described: N-butyl-2-benzylamino-propionamide and -butyramide, N<SP>1</SP>-butyl-N<SP>2</SP>-benzyl-1,2-propanediamine and -1,2-butanediamine,and N<SP>1</SP>-butyl-1,2-propane diamine and -1,2-butane-diamine. N-Butyl-andbenzyl-2-chloro-propionamides are obtained by reacting 2-chloro-propionyl chloride with butyl amine or benzylamine (N-butyl-2-chloro-butyramide is similarly obtained); N-benzyl-2-tert.- butylamino -propionamide, N<SP>1</SP>-benzyl-N<SP>2</SP>-tert.- butyl-1,2-propanediamine and N<SP>2</SP>-tert.-butyl-1,2- propane diamine hydrobromide are also described. Pharmaceutical preparations showing hypoglycaemic action contain I as active-ingredient; administration may be orally or parenterally.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH388168A CH504443A (en) | 1968-03-14 | 1968-03-14 | Hypoglycaemic sulphanilamide derivs. |
| CH388368A CH504444A (en) | 1968-03-14 | 1968-03-14 | Hypoglycaemic sulphanilamide derivs. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1263561A true GB1263561A (en) | 1972-02-09 |
Family
ID=25694076
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB03513/69A Expired GB1263561A (en) | 1968-03-14 | 1969-03-14 | New sulphanilamide derivatives, their production and compositions containing same |
Country Status (11)
| Country | Link |
|---|---|
| BE (1) | BE729834A (en) |
| BG (3) | BG16747A3 (en) |
| DE (1) | DE1912849A1 (en) |
| DK (1) | DK125323B (en) |
| FR (1) | FR2003885A1 (en) |
| GB (1) | GB1263561A (en) |
| IE (1) | IE32985B1 (en) |
| IL (1) | IL31801A (en) |
| NL (1) | NL6903830A (en) |
| NO (1) | NO123805B (en) |
| SE (1) | SE354070B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8517854D0 (en) * | 1985-07-15 | 1985-08-21 | Roussell Lab Ltd | Chemical compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1224812A (en) * | 1956-12-28 | 1960-06-27 | Geigy Ag J R | Novel 2-imino-1.3-di-n-heterocycles and their preparation process |
-
1969
- 1969-03-07 DK DK127469AA patent/DK125323B/en unknown
- 1969-03-07 SE SE03168/69A patent/SE354070B/xx unknown
- 1969-03-07 NO NO0965/69A patent/NO123805B/no unknown
- 1969-03-12 NL NL6903830A patent/NL6903830A/xx unknown
- 1969-03-13 FR FR6907107A patent/FR2003885A1/fr not_active Withdrawn
- 1969-03-13 BG BG012265A patent/BG16747A3/en unknown
- 1969-03-13 BG BG011841A patent/BG15572A3/en unknown
- 1969-03-13 BE BE729834D patent/BE729834A/xx unknown
- 1969-03-13 DE DE19691912849 patent/DE1912849A1/en active Pending
- 1969-03-13 IE IE331/69A patent/IE32985B1/en unknown
- 1969-03-13 IL IL31801A patent/IL31801A/en unknown
- 1969-03-13 BG BG012266A patent/BG17009A3/en unknown
- 1969-03-14 GB GB03513/69A patent/GB1263561A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK125323C (en) | 1973-07-23 |
| IE32985L (en) | 1969-09-14 |
| NO123805B (en) | 1972-01-17 |
| BG17009A3 (en) | 1973-04-25 |
| NL6903830A (en) | 1969-09-16 |
| BE729834A (en) | 1969-09-15 |
| IE32985B1 (en) | 1974-02-06 |
| DE1912849A1 (en) | 1969-10-02 |
| DK125323B (en) | 1973-02-05 |
| IL31801A0 (en) | 1969-05-28 |
| IL31801A (en) | 1972-09-28 |
| BG16747A3 (en) | 1973-02-15 |
| BG15572A3 (en) | 1976-06-21 |
| SE354070B (en) | 1973-02-26 |
| FR2003885A1 (en) | 1969-11-14 |
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