DE2545329A1 - 1-amid-alkyl-4-sulfonyl-piperazin-derivate - Google Patents
1-amid-alkyl-4-sulfonyl-piperazin-derivateInfo
- Publication number
- DE2545329A1 DE2545329A1 DE19752545329 DE2545329A DE2545329A1 DE 2545329 A1 DE2545329 A1 DE 2545329A1 DE 19752545329 DE19752545329 DE 19752545329 DE 2545329 A DE2545329 A DE 2545329A DE 2545329 A1 DE2545329 A1 DE 2545329A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- sulfonyl
- amide
- original
- stage
- 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.)
- Pending
Links
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title claims description 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- ZECNLXUZYQZMAL-UHFFFAOYSA-N 2-sulfonylpiperazine Chemical compound O=S(=O)=C1CNCCN1 ZECNLXUZYQZMAL-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- FXLVCHSCGBTGPL-UHFFFAOYSA-N 1-benzylsulfonylpiperazine Chemical compound C1CNCCN1S(=O)(=O)CC1=CC=CC=C1 FXLVCHSCGBTGPL-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000002526 effect on cardiovascular system Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229960005141 piperazine Drugs 0.000 description 2
- 229960003506 piperazine hexahydrate Drugs 0.000 description 2
- AVRVZRUEXIEGMP-UHFFFAOYSA-N piperazine;hexahydrate Chemical compound O.O.O.O.O.O.C1CNCCN1 AVRVZRUEXIEGMP-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 241001136792 Alle Species 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 230000002057 chronotropic effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000000297 inotrophic effect Effects 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- -1 monocamphor sulfonylpiperazine Chemical compound 0.000 description 1
- 230000001129 nonadrenergic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000004526 pharmaceutical effect Effects 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- YGIYXPDSUCRWCW-UHFFFAOYSA-N sulfuryl dichloride;4,7,7-trimethylbicyclo[2.2.1]heptan-3-one Chemical compound ClS(Cl)(=O)=O.C1CC2(C)C(=O)CC1C2(C)C YGIYXPDSUCRWCW-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 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
- C07D295/22—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 hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES432334A ES432334A1 (es) | 1974-11-27 | 1974-11-27 | Procedimiento de obtencion de derivados 1-amido alquil-4- sulfonil-piperazina. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2545329A1 true DE2545329A1 (de) | 1976-08-12 |
Family
ID=8468076
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752545329 Pending DE2545329A1 (de) | 1974-11-27 | 1975-10-09 | 1-amid-alkyl-4-sulfonyl-piperazin-derivate |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5165778A (cg-RX-API-DMAC7.html) |
| CH (1) | CH605833A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE2545329A1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES432334A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2292477A1 (cg-RX-API-DMAC7.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001058436A1 (en) * | 2000-02-11 | 2001-08-16 | Genomine, Inc. | Antagonists for nicotinic acetylcholine receptor, which are containing borneol or camphor as an active ingredient |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56157809U (cg-RX-API-DMAC7.html) * | 1980-04-24 | 1981-11-25 | ||
| US5648352A (en) * | 1991-09-13 | 1997-07-15 | Merck & Co., Inc. | Piperazinylcamphorsulfonyl oxytocin antagonists |
| EP0533241A3 (en) * | 1991-09-16 | 1993-09-29 | Merck & Co. Inc. | Substituted alkyl derivatives of piperazinylcamphorsulfonyl oxytocin antagonists |
| EP0533242A3 (en) * | 1991-09-16 | 1993-09-15 | Merck & Co. Inc. | Substituted derivatives of piperazinylcamphorsulfonyl oxytocin antagonists |
| EP0533240A3 (en) * | 1991-09-16 | 1993-09-29 | Merck & Co. Inc. | Substituted amine derivatives of piperazinylcamphorsulfonyl oxytocin antagonists |
| AU691829B2 (en) * | 1993-07-16 | 1998-05-28 | Merck & Co., Inc. | Benzoxazinone and benzopyrimidinone piperidinyl tocolytic oxytocin receptor antagonists |
| US5686454A (en) * | 1993-07-16 | 1997-11-11 | Merck & Co., Inc. | Camphorcarbonyl |
| US5464788A (en) * | 1994-03-24 | 1995-11-07 | Merck & Co., Inc. | Tocolytic oxytocin receptor antagonists |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES374515A1 (es) * | 1969-12-12 | 1972-01-01 | Liade Sa Lab | Procedimiento de obtencion de nuevos compuestos con accio- nes cardiovasculares. |
-
1974
- 1974-11-27 ES ES432334A patent/ES432334A1/es not_active Expired
-
1975
- 1975-03-27 JP JP50036149A patent/JPS5165778A/ja active Granted
- 1975-10-02 FR FR7530224A patent/FR2292477A1/fr active Granted
- 1975-10-09 DE DE19752545329 patent/DE2545329A1/de active Pending
- 1975-10-20 CH CH1358675A patent/CH605833A5/xx not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001058436A1 (en) * | 2000-02-11 | 2001-08-16 | Genomine, Inc. | Antagonists for nicotinic acetylcholine receptor, which are containing borneol or camphor as an active ingredient |
Also Published As
| Publication number | Publication date |
|---|---|
| CH605833A5 (cg-RX-API-DMAC7.html) | 1978-10-13 |
| FR2292477A1 (fr) | 1976-06-25 |
| JPS5165778A (en) | 1976-06-07 |
| JPS541317B2 (cg-RX-API-DMAC7.html) | 1979-01-23 |
| FR2292477B1 (cg-RX-API-DMAC7.html) | 1979-09-14 |
| ES432334A1 (es) | 1976-11-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHW | Rejection |