ES338403A1 - Sulphanilamide Derivatives and Process for Their Production - Google Patents
Sulphanilamide Derivatives and Process for Their ProductionInfo
- Publication number
- ES338403A1 ES338403A1 ES338403A ES338403A ES338403A1 ES 338403 A1 ES338403 A1 ES 338403A1 ES 338403 A ES338403 A ES 338403A ES 338403 A ES338403 A ES 338403A ES 338403 A1 ES338403 A1 ES 338403A1
- Authority
- ES
- Spain
- Prior art keywords
- formula
- monocycloaliphatic
- reaction
- amino
- group
- 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
- 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
- 150000003839 salts Chemical class 0.000 abstract 5
- 238000006243 chemical reaction Methods 0.000 abstract 4
- 150000007522 mineralic acids Chemical class 0.000 abstract 3
- 150000007524 organic acids Chemical class 0.000 abstract 3
- DISXFZWKRTZTRI-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-amine Chemical class NC1=NCCN1 DISXFZWKRTZTRI-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- PZZRSEUDGCFXIH-UHFFFAOYSA-N 2-methylsulfanyl-4,5-dihydro-1h-imidazol-1-ium;iodide Chemical class I.CSC1=NCCN1 PZZRSEUDGCFXIH-UHFFFAOYSA-N 0.000 abstract 1
- 101710178035 Chorismate synthase 2 Proteins 0.000 abstract 1
- 101710152694 Cysteine synthase 2 Proteins 0.000 abstract 1
- -1 N-(2-substituted amino-ethyl)-guanidine Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 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
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 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
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
- C07D235/24—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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Novel compounds of formula (wherein R is C 1-5 alkyl, a monocycloaliphatic hydrocarbon group of up to 10 carbon atoms optionally substituted by one or two C 1-3 alkyl groups, or a monocycloaliphatic hydrocarbonmethyl or -ethyl group wherein the monocycloaliphatic radical contains up to 10 carbon atoms) and their pharmaceutically acceptable addition salts with organic or inorganic acids, are prepared by reacting a reactive functional derivative of a para-X-benzenesulphonic acid (wherein X is a radical convertible into an amino group by hydrolysis, reduction or reductive cleavage) with a compound of formula or with an acid addition salt of such a compound in the presence of an acid binding agent, converting the group X in the product to amino, and if desired salifying the resulting compound of Formula I with an appropriate organic or inorganic acid. 2 - Amino - 2 - imidazolines of Formula III are prepared from 2-imino-imidazolidine by reaction with an alkyl halide or monocycloaliphatic halide, or from N-(R)-ethylenediamines (i) by reaction with cyanogen chloride, or (ii) by reaction with CS 2 to form 1-(R)- imidazolidine - 2 - thiones which are converted with CH 3 I into 2-methylthio-2-imidazolinium iodides which are reacted with ammonia, or (iii) by reaction with a salt of S-methyl-isothiourea and heating the resulting salt of an N-(2-substituted amino-ethyl)-guanidine. The compounds of Formula I and their pharmaceutically acceptable salts with organic and inorganic acids are stated to possess hypoglycaemic activity and may be made up with carriers into pharmaceutical compositions suitable for oral or parenteral administration.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH428066A CH470397A (en) | 1966-03-24 | 1966-03-24 | Process for the preparation of new derivatives of sulfanilamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES338403A1 true ES338403A1 (en) | 1968-04-01 |
Family
ID=4273162
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES338403A Expired ES338403A1 (en) | 1966-03-24 | 1967-03-23 | Sulphanilamide Derivatives and Process for Their Production |
Country Status (12)
| Country | Link |
|---|---|
| AT (1) | AT266121B (en) |
| CH (1) | CH470397A (en) |
| DE (1) | DE1695014A1 (en) |
| DK (1) | DK116133B (en) |
| ES (1) | ES338403A1 (en) |
| FI (1) | FI48081C (en) |
| FR (2) | FR1586813A (en) |
| GB (1) | GB1174152A (en) |
| GR (1) | GR36364B (en) |
| IL (1) | IL27674A (en) |
| NO (1) | NO121400B (en) |
| SE (1) | SE339476B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL231063B1 (en) | 2013-04-10 | 2019-01-31 | Oncoarendi Therapeutics Spolka Z Ograniczona Odpowiedzialnoscia | Derivatives of 1-(substituted sulfonyl) 2-aminoimidazoline as an anticancer and antiproliferative agents |
-
1966
- 1966-03-24 CH CH428066A patent/CH470397A/en not_active IP Right Cessation
-
1967
- 1967-03-20 FI FI82667A patent/FI48081C/en active
- 1967-03-22 DK DK154367A patent/DK116133B/en unknown
- 1967-03-22 NO NO16742267A patent/NO121400B/no unknown
- 1967-03-23 ES ES338403A patent/ES338403A1/en not_active Expired
- 1967-03-23 AT AT280467A patent/AT266121B/en active
- 1967-03-23 DE DE19671695014 patent/DE1695014A1/en active Pending
- 1967-03-23 GR GR670136364A patent/GR36364B/en unknown
- 1967-03-23 GB GB03708/67A patent/GB1174152A/en not_active Expired
- 1967-03-23 SE SE412067A patent/SE339476B/xx unknown
- 1967-03-23 IL IL2767467A patent/IL27674A/en unknown
- 1967-03-24 FR FR1586813D patent/FR1586813A/fr not_active Expired
- 1967-06-23 FR FR111636A patent/FR6520M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI48081B (en) | 1974-02-28 |
| SE339476B (en) | 1971-10-11 |
| DK116133B (en) | 1969-12-15 |
| NO121400B (en) | 1971-02-22 |
| FR1586813A (en) | 1970-03-06 |
| CH470397A (en) | 1969-03-31 |
| GR36364B (en) | 1969-02-04 |
| DE1695014A1 (en) | 1972-04-27 |
| FI48081C (en) | 1974-06-10 |
| FR6520M (en) | 1968-12-09 |
| AT266121B (en) | 1968-11-11 |
| IL27674A (en) | 1971-05-26 |
| GB1174152A (en) | 1969-12-17 |
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