DE2001144A1 - Ketonderivate von 1-(2-Hydroxyaethyl)-piperazin - Google Patents
Ketonderivate von 1-(2-Hydroxyaethyl)-piperazinInfo
- Publication number
- DE2001144A1 DE2001144A1 DE19702001144 DE2001144A DE2001144A1 DE 2001144 A1 DE2001144 A1 DE 2001144A1 DE 19702001144 DE19702001144 DE 19702001144 DE 2001144 A DE2001144 A DE 2001144A DE 2001144 A1 DE2001144 A1 DE 2001144A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- rac
- ketones
- product
- phil
- 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
- -1 Ketone derivatives of 1- (2-hydroxyethyl) piperazine Chemical class 0.000 title description 2
- 238000000034 method Methods 0.000 claims description 13
- 150000002576 ketones Chemical class 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 230000000701 neuroleptic effect Effects 0.000 claims description 9
- 239000003176 neuroleptic agent Substances 0.000 claims description 8
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000000829 suppository Substances 0.000 claims description 4
- 239000002562 thickening agent Substances 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- 235000015165 citric acid Nutrition 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 229940102223 injectable solution Drugs 0.000 claims description 2
- 239000004310 lactic acid Substances 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- 239000011975 tartaric acid Substances 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- 229940035676 analgesics Drugs 0.000 claims 1
- 239000000730 antalgic agent Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 33
- 241001465754 Metazoa Species 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 7
- 241000700159 Rattus Species 0.000 description 7
- 229940025084 amphetamine Drugs 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 229960000212 aminophenazone Drugs 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 208000011580 syndromic disease Diseases 0.000 description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- 239000005995 Aluminium silicate Substances 0.000 description 3
- 206010015995 Eyelid ptosis Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 230000006399 behavior Effects 0.000 description 3
- 230000002903 catalepsic effect Effects 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 201000003004 ptosis Diseases 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 208000009132 Catalepsy Diseases 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 241000700157 Rattus norvegicus Species 0.000 description 2
- 206010047853 Waxy flexibility Diseases 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000007928 intraperitoneal injection Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- BFTGQIQVUVTBJU-UHFFFAOYSA-N 5,6-dihydroimidazo[2,1-c][1,2,4]dithiazole-3-thione Chemical compound C1CN2C(=S)SSC2=N1 BFTGQIQVUVTBJU-UHFFFAOYSA-N 0.000 description 1
- 206010001497 Agitation Diseases 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 208000012639 Balance disease Diseases 0.000 description 1
- 208000005171 Dysmenorrhea Diseases 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241000581650 Ivesia Species 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 206010036030 Polyarthritis Diseases 0.000 description 1
- 208000001431 Psychomotor Agitation Diseases 0.000 description 1
- 208000012545 Psychophysiologic disease Diseases 0.000 description 1
- 206010038743 Restlessness Diseases 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 238000005162 X-ray Laue diffraction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 208000012826 adjustment disease Diseases 0.000 description 1
- 210000004100 adrenal gland Anatomy 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 206010003549 asthenia Diseases 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000020375 flavoured syrup Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 238000010562 histological examination Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000037023 motor activity Effects 0.000 description 1
- 231100000926 not very toxic Toxicity 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- 229940102708 phenylbutazone 100 mg Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 230000004620 sleep latency Effects 0.000 description 1
- SQMCFUSVGSBKFK-UHFFFAOYSA-M sodium;5-(cyclohexen-1-yl)-1,5-dimethylpyrimidin-3-ide-2,4,6-trione Chemical compound [Na+].O=C1N(C)C(=O)[N-]C(=O)C1(C)C1=CCCCC1 SQMCFUSVGSBKFK-UHFFFAOYSA-M 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000007666 subchronic toxicity Effects 0.000 description 1
- 231100000195 subchronic toxicity Toxicity 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
- 210000002700 urine Anatomy 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
- C07D295/04—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
- C07D295/10—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 doubly bound oxygen or sulphur atoms
- C07D295/104—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 doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/108—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 doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR6900630A FR2028047B1 (enrdf_load_stackoverflow) | 1969-01-16 | 1969-01-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2001144A1 true DE2001144A1 (de) | 1970-07-23 |
Family
ID=9027881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702001144 Pending DE2001144A1 (de) | 1969-01-16 | 1970-01-12 | Ketonderivate von 1-(2-Hydroxyaethyl)-piperazin |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE743969A (enrdf_load_stackoverflow) |
| DE (1) | DE2001144A1 (enrdf_load_stackoverflow) |
| ES (1) | ES375495A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2028047B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1261004A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4836181A (enrdf_load_stackoverflow) * | 1971-09-13 | 1973-05-28 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2206088A1 (en) * | 1972-11-14 | 1974-06-07 | Synthelabo | Analgesic piperazino butyrophenone ketals - prepd. by reaction of halo butyrophenone ketal with hydroxy alkyl piperazine |
| WO2006074192A2 (en) * | 2005-01-03 | 2006-07-13 | Bionaut Pharmaceuticals, Inc. | Treatment of inflammatory disorders |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1481001A (fr) * | 1959-07-01 | 1967-05-19 | Procédé de préparation des dérivés de la phénacyl-pipérazine |
-
1969
- 1969-01-16 FR FR6900630A patent/FR2028047B1/fr not_active Expired
- 1969-12-31 BE BE743969D patent/BE743969A/xx unknown
-
1970
- 1970-01-12 DE DE19702001144 patent/DE2001144A1/de active Pending
- 1970-01-15 GB GB211070A patent/GB1261004A/en not_active Expired
- 1970-01-16 ES ES375495A patent/ES375495A1/es not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4836181A (enrdf_load_stackoverflow) * | 1971-09-13 | 1973-05-28 |
Also Published As
| Publication number | Publication date |
|---|---|
| BE743969A (enrdf_load_stackoverflow) | 1970-05-28 |
| GB1261004A (en) | 1972-01-19 |
| ES375495A1 (es) | 1972-05-16 |
| FR2028047A1 (enrdf_load_stackoverflow) | 1970-10-09 |
| FR2028047B1 (enrdf_load_stackoverflow) | 1974-10-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3751006T2 (de) | Psychostimulierendes mittel. | |
| CH635823A5 (de) | Verfahren zur herstellung von neuen 1-amidin-3-substituierten-phenylharnstoffen. | |
| DE1795769A1 (de) | Tetrahydrohomopyrimidazolderivate, deren saeureadditionssalze und quaternaeren salze sowie verfahren zu deren herstellung | |
| DE2446010A1 (de) | 4-(monoalkylamino)benzoesaeurederivate und verfahren zu ihrer herstellung | |
| DE1568759C3 (de) | Verwendung von 4-Guanidino-butyramid bei der Behandlung von diabetischen Zuständen | |
| DE2118109A1 (de) | Neue chemische Verbindung | |
| DE2006895A1 (de) | Neue Phenacetylguanidine und Verfahren zu ihrer Herstellung | |
| DE2001144A1 (de) | Ketonderivate von 1-(2-Hydroxyaethyl)-piperazin | |
| DE2851416A1 (de) | 2-(4-biphenylyl)-n-(diethylaminoalkyl)- propionamide, verfahren zu ihrer herstellung und diese enthaltende arzneimittel | |
| DE2157272B2 (de) | Verwendung von bis-(p-Chlorphenoxy)acetylharnstoff | |
| DE2313256C3 (de) | l^-Benzisoxazol-3-acetamidoxim, seine Salze, Verfahren zu seiner Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2527628C3 (de) | N-Vinyloxyäthyl-a-methyl-ß- phenäthylamine und Appetitzügler auf deren Basis | |
| DE3310584C2 (enrdf_load_stackoverflow) | ||
| DE2522218A1 (de) | Therapeutische zusammensetzung, methylaminderivate und verfahren zu deren herstellung | |
| CH579565A5 (en) | Imidazolin-2-ylamino-2,1,3-benzothiadiazoles prodn. - by cyclising corresp. beta aminoethyl (thio) ureas, active against muscle tremors and rigor | |
| DE1931927A1 (de) | Neue Cyclohexylaminderivate | |
| DE2511802A1 (de) | Alkoxyanilide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| DE3586150T2 (de) | Amidderivate der 2-(p-aminobenzyl)-buttersaeure und ihrer ester mit blutfettgehaltsenkender wirkung. | |
| DE1927786A1 (de) | Neue organische Verbindungen und Verfahren zu ihrer Herstellung | |
| DE1645901C3 (de) | gamma-(4-Alkylp!peridino)-p-fluorbutyrophenone und Verfahren zu ihrer Herstellung | |
| DE1921651A1 (de) | Verfahren zur Herstellung von neuen,substituierten Phenylalkansaeuren | |
| DE2433837B2 (de) | 1-Amidino-3-phenyl-harnstoffe, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende therapeutische Zubereitungen | |
| DE2017023A1 (de) | Nitroimidazolyl-nitrone | |
| AT326109B (de) | Verfahren zur herstellung von neuen n,n'-bis-(beta-hydroxy-beta-arylathyl)-diaminoalkanen | |
| DE924985C (de) | Verfahren zur Herstellung von 3, 4-Dioxy-ª-isopropylaminopropiophenon und seinen mit Saeuren gebildeten Salzen |