DE2714148C3 - 1-(Naphthylmethyl)-4-thiazolylpipirazine, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel - Google Patents
1-(Naphthylmethyl)-4-thiazolylpipirazine, Verfahren zu ihrer Herstellung und sie enthaltende ArzneimittelInfo
- Publication number
- DE2714148C3 DE2714148C3 DE2714148A DE2714148A DE2714148C3 DE 2714148 C3 DE2714148 C3 DE 2714148C3 DE 2714148 A DE2714148 A DE 2714148A DE 2714148 A DE2714148 A DE 2714148A DE 2714148 C3 DE2714148 C3 DE 2714148C3
- Authority
- DE
- Germany
- Prior art keywords
- piperazine
- acid
- thiazolyl
- naphthylmethyl
- preparation
- 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 claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000003814 drug Substances 0.000 title description 3
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- CNHONDQAIRWONL-UHFFFAOYSA-N 2-[4-(naphthalen-2-ylmethyl)piperazin-1-yl]-1,3-thiazole Chemical compound C=1C=C2C=CC=CC2=CC=1CN(CC1)CCN1C1=NC=CS1 CNHONDQAIRWONL-UHFFFAOYSA-N 0.000 claims description 4
- NKLSWPXTPKLYMP-UHFFFAOYSA-N 2-[4-(naphthalen-1-ylmethyl)piperazin-1-yl]-1,3-thiazole Chemical compound C=1C=CC2=CC=CC=C2C=1CN(CC1)CCN1C1=NC=CS1 NKLSWPXTPKLYMP-UHFFFAOYSA-N 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WQFWIVTXNKRNJZ-UHFFFAOYSA-N 2-piperazin-1-yl-1,3-thiazole Chemical compound C1CNCCN1C1=NC=CS1 WQFWIVTXNKRNJZ-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000007912 intraperitoneal administration Methods 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000000926 neurological effect Effects 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- KLEYVGWAORGTIT-UHFFFAOYSA-N 2-chlorothiazole Chemical compound ClC1=NC=CS1 KLEYVGWAORGTIT-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 description 2
- 229960002802 bromocriptine Drugs 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RZJGKPNCYQZFGR-UHFFFAOYSA-N 1-(bromomethyl)naphthalene Chemical compound C1=CC=C2C(CBr)=CC=CC2=C1 RZJGKPNCYQZFGR-UHFFFAOYSA-N 0.000 description 1
- HGYDREHWXXUUIS-UHFFFAOYSA-N 1-(naphthalen-1-ylmethyl)piperazine Chemical compound C=1C=CC2=CC=CC=C2C=1CN1CCNCC1 HGYDREHWXXUUIS-UHFFFAOYSA-N 0.000 description 1
- FDVCUOJHWRHXMF-UHFFFAOYSA-N 1-(naphthalen-2-ylmethyl)piperazine Chemical compound C=1C=C2C=CC=CC2=CC=1CN1CCNCC1 FDVCUOJHWRHXMF-UHFFFAOYSA-N 0.000 description 1
- RUHJZSZTSCSTCC-UHFFFAOYSA-N 2-(bromomethyl)naphthalene Chemical compound C1=CC=CC2=CC(CBr)=CC=C21 RUHJZSZTSCSTCC-UHFFFAOYSA-N 0.000 description 1
- JJIXVEDQDDUZQT-UHFFFAOYSA-N 2-[4-(2H-chromen-6-ylmethyl)piperazin-1-yl]-1,3-thiazole Chemical compound C=1C=C2OCC=CC2=CC=1CN(CC1)CCN1C1=NC=CS1 JJIXVEDQDDUZQT-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000008431 aliphatic amides Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- -1 alkali metal salts Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229960002598 fumaric acid Drugs 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 229940045996 isethionic acid Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098895 maleic acid Drugs 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229940116315 oxalic acid Drugs 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000008014 pharmaceutical binder Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229940095574 propionic acid Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- 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)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB14811/76A GB1518559A (en) | 1976-04-12 | 1976-04-12 | Naphthyl derivatives processes for their preparation an pharmaceutical compositions containing them |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2714148A1 DE2714148A1 (de) | 1977-10-13 |
| DE2714148B2 DE2714148B2 (de) | 1980-08-07 |
| DE2714148C3 true DE2714148C3 (de) | 1981-11-05 |
Family
ID=10047906
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2714148A Expired DE2714148C3 (de) | 1976-04-12 | 1977-03-30 | 1-(Naphthylmethyl)-4-thiazolylpipirazine, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4112092A (enExample) |
| JP (1) | JPS52125180A (enExample) |
| AU (1) | AU505379B2 (enExample) |
| BE (1) | BE853513A (enExample) |
| DE (1) | DE2714148C3 (enExample) |
| ES (1) | ES457370A1 (enExample) |
| FI (1) | FI771097A7 (enExample) |
| FR (1) | FR2348212A1 (enExample) |
| GB (1) | GB1518559A (enExample) |
| GR (1) | GR61147B (enExample) |
| NL (1) | NL7703839A (enExample) |
| NZ (1) | NZ183783A (enExample) |
| PH (1) | PH13715A (enExample) |
| PT (1) | PT66418B (enExample) |
| SE (1) | SE7704055L (enExample) |
| ZA (1) | ZA772026B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2961406D1 (en) * | 1978-04-13 | 1982-01-28 | Science Union & Cie | Monosubstituted piperazines, processes for their preparation and pharmaceutical compositions containing them |
| US4367335A (en) * | 1981-08-03 | 1983-01-04 | Mead Johnson & Company | Thiazolidinylalkylene piperazine derivatives |
| FR2519986A1 (fr) * | 1982-01-21 | 1983-07-22 | Adir | Nouveaux derives de benzodioxine, leurs procedes de preparation et les compositions pharmaceutiques les renfermant |
| HUT41752A (en) * | 1984-11-30 | 1987-05-28 | Sandoz Ag | Process for producing piperazine derivatives and pharmaceutical compositions containing them |
| US5801186A (en) | 1987-11-20 | 1998-09-01 | Hoechst Marion Roussel, Inc. | 3- 4-(1-substituted-4-piperazinyl)butyl!-4-thiazolidinone and related compounds |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK133809B (da) * | 1971-08-03 | 1976-07-26 | Wander Ag Dr A | Analogifremgangsmåde til fremstilling af heterocycliske forbindelser. |
| DE2263211A1 (de) * | 1972-12-23 | 1974-07-04 | Boehringer Sohn Ingelheim | Neue arylpiperazine und verfahren zu ihrer herstellung |
| CH583232A5 (enExample) * | 1973-02-02 | 1976-12-31 | Wander Ag Dr A | |
| GB1407552A (en) * | 1973-04-02 | 1975-09-24 | Science Union & Cie | Disubstituted piperazines processes for their preparation and pharmaceutical compositions containing them |
| GB1432660A (en) * | 1973-10-30 | 1976-04-22 | Science Union & Cie | Piperazine derivatives processes for their preparation and and pharamacueitcal compositions containing them |
-
1976
- 1976-04-12 GB GB14811/76A patent/GB1518559A/en not_active Expired
-
1977
- 1977-03-30 ES ES457370A patent/ES457370A1/es not_active Expired
- 1977-03-30 DE DE2714148A patent/DE2714148C3/de not_active Expired
- 1977-04-04 ZA ZA00772026A patent/ZA772026B/xx unknown
- 1977-04-04 NZ NZ183783A patent/NZ183783A/xx unknown
- 1977-04-06 FI FI771097A patent/FI771097A7/fi not_active Application Discontinuation
- 1977-04-06 SE SE7704055A patent/SE7704055L/xx unknown
- 1977-04-07 NL NL7703839A patent/NL7703839A/xx not_active Application Discontinuation
- 1977-04-07 GR GR53192A patent/GR61147B/el unknown
- 1977-04-07 AU AU24090/77A patent/AU505379B2/en not_active Expired
- 1977-04-08 FR FR7710686A patent/FR2348212A1/fr active Granted
- 1977-04-08 US US05/785,855 patent/US4112092A/en not_active Expired - Lifetime
- 1977-04-11 PT PT66418A patent/PT66418B/pt unknown
- 1977-04-11 JP JP4126077A patent/JPS52125180A/ja active Pending
- 1977-04-12 BE BE176642A patent/BE853513A/xx unknown
- 1977-04-12 PH PH19650A patent/PH13715A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1518559A (en) | 1978-07-19 |
| NZ183783A (en) | 1979-03-28 |
| PT66418B (fr) | 1978-09-18 |
| DE2714148A1 (de) | 1977-10-13 |
| SE7704055L (sv) | 1977-10-13 |
| AU2409077A (en) | 1978-10-12 |
| BE853513A (fr) | 1977-10-12 |
| PT66418A (fr) | 1977-05-01 |
| NL7703839A (nl) | 1977-10-14 |
| ZA772026B (en) | 1978-05-30 |
| FI771097A7 (enExample) | 1977-10-13 |
| FR2348212A1 (fr) | 1977-11-10 |
| GR61147B (en) | 1978-09-27 |
| FR2348212B1 (enExample) | 1980-03-28 |
| JPS52125180A (en) | 1977-10-20 |
| DE2714148B2 (de) | 1980-08-07 |
| ES457370A1 (es) | 1978-02-01 |
| PH13715A (en) | 1980-09-09 |
| AU505379B2 (en) | 1979-11-15 |
| US4112092A (en) | 1978-09-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0136658B1 (de) | 1-Benzyl-aminoalkyl-pyrrolidinone und ihre Säureadditionssalze, Verfahren zu ihrer Herstellung und Arzneimittel | |
| DE69014351T2 (de) | Pyridincarbonsäureamid-Derivate und diese enthaltende pharmazeutische Zusammensetzungen. | |
| DE69015842T2 (de) | Nicotinsäurederivate und diese enthaltende pharmazeutische Zusammensetzungen. | |
| DE3342164C2 (enExample) | ||
| DE2415082C3 (de) | 1 -{Cumaran-5-yl-methyl)-piperazine, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| CH649287A5 (de) | Carboximid-derivate, verfahren zur herstellung derselben sowie solche carboximid-derivate enthaltende medikamente. | |
| DE2429253A1 (de) | Phenylalkanolamine | |
| DE2238504B2 (de) | l-Phenoxy-3-alkylaminopropan-2-ol -Derivate | |
| DE10138273A1 (de) | Arzneimittel mit neuroprotektiver Wirkung | |
| DE2316920B2 (de) | Benzo eckige klammer auf d eckige klammer zu eckige klammer auf 1,3 eckige klammer zu dioxolderivate, deren herstellung und diese enthaltende arzneimittel | |
| CH649995A5 (de) | Piperazinderivate, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten. | |
| DE3420193A1 (de) | Neue substituierte pyrrolidinone, verfahren zu ihrer herstellung und arzneimittel | |
| EP0185909B1 (de) | 5-Alkyl-1-phenyl-2-piperazinoalkylpyrazolin-3-on-Verbindungen sowie Verfahren und Zwischenprodukte zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2512109A1 (de) | Hexahydro-gamma-carbolinderivate, deren salze, verfahren zu ihrer herstellung und arzneipraeparate | |
| DE2714148C3 (de) | 1-(Naphthylmethyl)-4-thiazolylpipirazine, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel | |
| DE3326724A1 (de) | In 1-stellung substituierte 4-hydroxymethyl-pyrrolidinone, verfahren zu ihrer herstellung, pharmazeutische zusammensetzungen und zwischenprodukte | |
| DE1670305C3 (de) | 5-Phenyl-2,4-dioxo-1,2,3,4-tetrahydro-3H-1,5-benzodiazepine und Verfahren zu ihrer Herstellung | |
| DE2630637C2 (de) | Sulfamylbenzylaminderivate, Verfahren zu ihrer Herstellung und Arzneimittel, die diese Verbindungen enthalten | |
| EP1317430B1 (de) | (2-azabicyclo [2.2.1]hept-7-yl)methanol-derivate als nikotinische acetylcholinrezeptor agonisten | |
| DE69115954T2 (de) | Kondensierte 7-gliedrige zyklische Verbindungen und diese enthaltende antipsychotische Zubereitung | |
| EP0018360A1 (de) | N-(5-Methoxybentofuran-2-ylcarbonyl)-N'-benzylpiperazin und Verfahren zu dessen Herstellung. | |
| DE2106038C3 (de) | 2-Imidazolin-2-ylamino-benzo [b] thiophene und diese enthaltende pharmazeutische Präparate | |
| CH651027A5 (de) | Heterocyclische verbindungen, ihre herstellung und verwendung. | |
| DE2313256C3 (de) | l^-Benzisoxazol-3-acetamidoxim, seine Salze, Verfahren zu seiner Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE1915230B2 (de) | Hydroxyphenylalkylaminderivate, verfahren zu deren herstellung und arzneimittel auf deren basis |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |