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)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (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 (enrdf_load_html_response) |
| CH (1) | CH605833A5 (enrdf_load_html_response) |
| DE (1) | DE2545329A1 (enrdf_load_html_response) |
| ES (1) | ES432334A1 (enrdf_load_html_response) |
| FR (1) | FR2292477A1 (enrdf_load_html_response) |
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 (enrdf_load_html_response) * | 1980-04-24 | 1981-11-25 | ||
| US5648352A (en) * | 1991-09-13 | 1997-07-15 | Merck & Co., Inc. | 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 |
| EP0533241A3 (en) * | 1991-09-16 | 1993-09-29 | Merck & Co. Inc. | Substituted alkyl derivatives of piperazinylcamphorsulfonyl oxytocin antagonists |
| CA2166975C (en) * | 1993-07-16 | 2005-04-05 | Mark G. Bock | Benzoxazinone and benzopyrimidinone piperidinyl tocolytic oxytocin receptor antagonists |
| JPH09500133A (ja) * | 1993-07-16 | 1997-01-07 | メルク エンド カンパニー インコーポレーテッド | オキシトシンのアンタゴニストである置換ピペラジニル樟脳誘導体 |
| 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 |
|---|---|
| FR2292477B1 (enrdf_load_html_response) | 1979-09-14 |
| FR2292477A1 (fr) | 1976-06-25 |
| JPS541317B2 (enrdf_load_html_response) | 1979-01-23 |
| ES432334A1 (es) | 1976-11-01 |
| JPS5165778A (en) | 1976-06-07 |
| CH605833A5 (enrdf_load_html_response) | 1978-10-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHW | Rejection |