GB674325A - New therapeutically useful piperazine derivatives - Google Patents
New therapeutically useful piperazine derivativesInfo
- Publication number
- GB674325A GB674325A GB2324/49A GB232449A GB674325A GB 674325 A GB674325 A GB 674325A GB 2324/49 A GB2324/49 A GB 2324/49A GB 232449 A GB232449 A GB 232449A GB 674325 A GB674325 A GB 674325A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethyl
- methyl
- general formula
- action
- chloride
- 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
- 150000004885 piperazines Chemical class 0.000 title abstract 2
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 4
- -1 sulphonyl halide Chemical class 0.000 abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 239000007858 starting material Substances 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 229910006080 SO2X Inorganic materials 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- 230000001476 alcoholic effect Effects 0.000 abstract 2
- FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 150000002367 halogens Chemical group 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- NANQJUFFKXWVJR-UHFFFAOYSA-N 1-(benzenesulfonyl)piperazine Chemical compound C=1C=CC=CC=1S(=O)(=O)N1CCNCC1 NANQJUFFKXWVJR-UHFFFAOYSA-N 0.000 abstract 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 abstract 1
- 206010049771 Shock haemorrhagic Diseases 0.000 abstract 1
- 206010044541 Traumatic shock Diseases 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000002168 alkylating agent Substances 0.000 abstract 1
- 229940100198 alkylating agent Drugs 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 abstract 1
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 abstract 1
- YSPVHAUJXLGZHP-UHFFFAOYSA-N ethyl piperidine-1-carboxylate Chemical compound CCOC(=O)N1CCCCC1 YSPVHAUJXLGZHP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003840 hydrochlorides Chemical class 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 230000000472 traumatic effect Effects 0.000 abstract 1
Classifications
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Piperazine derivatives of the general formula <FORM:0674325/IV (b)/1> (wherein R and R1 represent alkyl radicals containing respectively not more than 4 and not more than 3 carbon atoms) and their salts are manufactured by condensing a sulphonyl halide R-SO2X(X=halogen) with an N-mono-substituted piperazine, or by cyclizing a compound of the general formula <FORM:0674325/IV (b)/2> (wherein X represents a halogen atom) by condensation with a primary amine R1NH2 or a secondary amine NH(R1)2, and in the latter case simultaneously or subsequently converting the resulting quaternary derivative into the desired tertiary base, or by the action of an alkylating agent (e.g. a methyl or ethyl halide or sulphonate) on a compound of the general formula <FORM:0674325/IV (b)/3> In all cases the products are, if desired, converted into salts, e.g. into their hydrochlorides by the action of alcoholic or ethereal hydrogen chloride on a solution of the base in an anhydrous organic solvent, or into their ethiodides by the action of ethyl iodide on a solution of the base in an inert organic solvent. The products are of therapeutic value in the treatment of traumatic and haemorrhagic shock. Examples illustrate the various processes as applied to the preparation of compounds in which R is ethyl, methyl, n- and iso-propyl and n-butyl, and R1 is ethyl, methyl and isopropyl. Alkanesulphondi-b -haloethylamides, used as starting materials in the second of the processes above, are obtainable by reaction of a sulphonyl halide R-SO2X with a secondary halogenated amine NH(CH2CH2X)2, or with diethanolamine followed by replacement of the hydroxy groups by halogen (e.g. by the action of thionyl chloride). In examples, methane- or ethane-sulphonyl chloride is heated with 2 : 21-dichlordiethylamine hydrochloride in acetone in the presence of sodium carbonate. N-Methane- and -ethane-sulphonylpiperazine, used as starting materials in the third process, are prepared by stirring methane- or ethane-sulphonyl chloride with N-carbethoxypiperazine in ether, and hydrolysing the product with aqueous alcoholic caustic soda. The Specification as open to inspection under Sect. 91 comprises also the manufacture of compounds of the general formula above in which R represents a phenyl radical which may be substituted by a methyl, ethyl, propyl, methoxy or ethoxy group or a halogen atom. Additional examples describe the preparation of compounds in which R is phenyl, p-tolyl, p-chlorophenyl and p-methoxyphenyl. N-Benzenesulphonylpiperazine, which is one of the starting materials, is prepared by reacting benzenesulphonyl chloride with N-carbethoxypiperidine and hydrolysing the product. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR674325X | 1948-03-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB674325A true GB674325A (en) | 1952-06-25 |
Family
ID=9018669
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2324/49A Expired GB674325A (en) | 1948-03-05 | 1949-01-27 | New therapeutically useful piperazine derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB674325A (en) |
-
1949
- 1949-01-27 GB GB2324/49A patent/GB674325A/en not_active Expired
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