GB1047044A - Piperazines and process for their manufacture - Google Patents
Piperazines and process for their manufactureInfo
- Publication number
- GB1047044A GB1047044A GB303364A GB303364A GB1047044A GB 1047044 A GB1047044 A GB 1047044A GB 303364 A GB303364 A GB 303364A GB 303364 A GB303364 A GB 303364A GB 1047044 A GB1047044 A GB 1047044A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- salt
- piperazine
- resulting
- quaternary
- 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
- 238000000034 method Methods 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000004885 piperazines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 8
- 150000003839 salts Chemical class 0.000 abstract 6
- 150000001204 N-oxides Chemical class 0.000 abstract 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 3
- -1 piperazine ethers Chemical class 0.000 abstract 3
- 239000002253 acid 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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 230000002908 adrenolytic effect Effects 0.000 abstract 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000003276 anti-hypertensive effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 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
- 239000002585 base Substances 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 239000002934 diuretic Substances 0.000 abstract 1
- 230000001882 diuretic effect Effects 0.000 abstract 1
- 239000008298 dragée Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000005059 halophenyl group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 abstract 1
- 230000000894 saliuretic effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 239000000829 suppository Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/092—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings with aromatic radicals attached to the chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises piperazine ethers of formula <F\1> where Ph is an unsubstituted phenyl group, R is C1- 7 alkyl, R1 is hydrogen or methyl, and Ar is phenyl, C1- 7 alkoxyphenyl, halophenyl or pyridyl, and N-oxides and quaternary ammonium compounds thereof, and also acid addition salts of the free bases and N-oxides. They are prepared by reacting a piperazine compound <F\2> or a salt thereof with a compound <F\3> where Y is a reactive ester group, e.g. a halide, sulphate or sulphonate, an acid acceptor which may be excess piperazine compound being used when the free base is employed. If desired a resulting salt may be converted to a free compound or another salt and/or a resulting compound into an N-oxide or quaternary compound and/or a resulting compound or N-oxide into a salt, and/or one quaternary compound into another, numerous methods being specified for these processes. Racemates may be resolved. The above compounds including organic and inorganic acid addition salts may be used in pharmaceutical compositions for oral, rectal and parenteral administration, e.g. capsules, tablets, dragees, suppositories, solutions, suspensions or emulsions. The compounds have anti-inflammatory antihypertensive, adrenolytic, diuretic and saliuretic activities.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25327063A | 1963-01-23 | 1963-01-23 | |
| US31534363A | 1963-10-10 | 1963-10-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1047044A true GB1047044A (en) | 1966-11-02 |
Family
ID=26943082
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB303264A Expired GB1048903A (en) | 1963-01-23 | 1964-01-23 | Piperazines and process for their manufacture |
| GB303364A Expired GB1047044A (en) | 1963-01-23 | 1964-01-23 | Piperazines and process for their manufacture |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB303264A Expired GB1048903A (en) | 1963-01-23 | 1964-01-23 | Piperazines and process for their manufacture |
Country Status (7)
| Country | Link |
|---|---|
| AT (10) | AT247342B (en) |
| BE (2) | BE642844A (en) |
| CH (6) | CH446346A (en) |
| ES (2) | ES295631A1 (en) |
| FR (2) | FR3308M (en) |
| GB (2) | GB1048903A (en) |
| NL (2) | NL6400467A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9911992A (en) * | 1998-06-30 | 2001-03-27 | Zeria Pharm Co Ltd | Derivatives of n-phenyl-n 'phenylpropylpiperazine and process for their preparation |
| USD1009638S1 (en) * | 2019-06-07 | 2024-01-02 | Seiko Epson Corporation | Packaging container |
| USD979418S1 (en) * | 2019-06-28 | 2023-02-28 | Seiko Epson Corporation | Packaging container |
-
1964
- 1964-01-20 CH CH555467A patent/CH446346A/en unknown
- 1964-01-20 CH CH60264A patent/CH446345A/en unknown
- 1964-01-20 CH CH555667A patent/CH446348A/en unknown
- 1964-01-20 CH CH555767A patent/CH446349A/en unknown
- 1964-01-20 CH CH60164A patent/CH449629A/en unknown
- 1964-01-20 CH CH555567A patent/CH446347A/en unknown
- 1964-01-22 AT AT715664A patent/AT247342B/en active
- 1964-01-22 AT AT716464A patent/AT247350B/en active
- 1964-01-22 NL NL6400467A patent/NL6400467A/xx unknown
- 1964-01-22 BE BE642844A patent/BE642844A/xx unknown
- 1964-01-22 AT AT716564A patent/AT247351B/en active
- 1964-01-22 AT AT716364A patent/AT247349B/en active
- 1964-01-22 AT AT716264A patent/AT247348B/en active
- 1964-01-22 AT AT716064A patent/AT247346B/en active
- 1964-01-22 AT AT49464A patent/AT247337B/en active
- 1964-01-22 NL NL6400466A patent/NL6400466A/xx unknown
- 1964-01-22 BE BE642845A patent/BE642845A/xx unknown
- 1964-01-22 AT AT49364A patent/AT247336B/en active
- 1964-01-22 AT AT716164A patent/AT247347B/en active
- 1964-01-22 AT AT715764A patent/AT247343B/en active
- 1964-01-23 GB GB303264A patent/GB1048903A/en not_active Expired
- 1964-01-23 ES ES295631A patent/ES295631A1/en not_active Expired
- 1964-01-23 ES ES295632A patent/ES295632A1/en not_active Expired
- 1964-01-23 GB GB303364A patent/GB1047044A/en not_active Expired
- 1964-04-14 FR FR970793A patent/FR3308M/en not_active Expired
- 1964-04-14 FR FR970794A patent/FR3309M/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT247346B (en) | 1966-06-10 |
| AT247351B (en) | 1966-06-10 |
| CH449629A (en) | 1968-01-15 |
| AT247343B (en) | 1966-06-10 |
| CH446345A (en) | 1967-11-15 |
| AT247336B (en) | 1966-06-10 |
| FR3308M (en) | 1965-05-10 |
| AT247337B (en) | 1966-06-10 |
| NL6400466A (en) | 1964-07-24 |
| AT247349B (en) | 1966-06-10 |
| CH446346A (en) | 1967-11-15 |
| ES295631A1 (en) | 1964-07-16 |
| AT247350B (en) | 1966-06-10 |
| AT247347B (en) | 1966-06-10 |
| BE642845A (en) | 1964-07-22 |
| GB1048903A (en) | 1966-11-23 |
| AT247342B (en) | 1966-06-10 |
| FR3309M (en) | 1965-05-10 |
| AT247348B (en) | 1966-06-10 |
| NL6400467A (en) | 1964-07-24 |
| CH446349A (en) | 1967-11-15 |
| BE642844A (en) | 1964-07-22 |
| CH446347A (en) | 1967-11-15 |
| ES295632A1 (en) | 1964-07-16 |
| CH446348A (en) | 1967-11-15 |
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