FI58495C - Analogifoerfarande foer framstaellning av terapeutiskt aktiv 1-(3-(4-m-klorfenyl-1-piperazinyl)-propyl)-3,4-dietyl- 2-1,2,4-triazolin-5-on och farmaceutiskt godtagbara salter daerav - Google Patents
Analogifoerfarande foer framstaellning av terapeutiskt aktiv 1-(3-(4-m-klorfenyl-1-piperazinyl)-propyl)-3,4-dietyl- 2-1,2,4-triazolin-5-on och farmaceutiskt godtagbara salter daerav Download PDFInfo
- Publication number
- FI58495C FI58495C FI3188/73A FI318873A FI58495C FI 58495 C FI58495 C FI 58495C FI 3188/73 A FI3188/73 A FI 3188/73A FI 318873 A FI318873 A FI 318873A FI 58495 C FI58495 C FI 58495C
- Authority
- FI
- Finland
- Prior art keywords
- triazolin
- diethyl
- treated
- therapeutic activities
- chloro
- Prior art date
Links
- 230000001225 therapeutic effect Effects 0.000 title claims description 4
- -1 4-m-chloro-phenyl-1-piperazinyl Chemical group 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 5
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 claims description 2
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 claims description 2
- 241000234282 Allium Species 0.000 claims 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 9
- 241000700159 Rattus Species 0.000 description 8
- VHFVKMTVMIZMIK-UHFFFAOYSA-N 1-(3-chlorophenyl)piperazine Chemical compound ClC1=CC=CC(N2CCNCC2)=C1 VHFVKMTVMIZMIK-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000003444 anaesthetic effect Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000001624 sedative effect Effects 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000037023 motor activity Effects 0.000 description 2
- 239000012053 oil suspension Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- NDQKGEFMUGSRNS-UHFFFAOYSA-N 1-(3-chlorophenyl)-4-(3-chloropropyl)piperazine Chemical compound C1CN(CCCCl)CCN1C1=CC=CC(Cl)=C1 NDQKGEFMUGSRNS-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- WBJWXIQDBDZMAW-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(O)=CC=C21 WBJWXIQDBDZMAW-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- ZHZYGIQVBQWOJJ-UHFFFAOYSA-N 3,4-dihydro-1,2,4-triazol-5-one Chemical compound O=C1NCN=N1 ZHZYGIQVBQWOJJ-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- PYHXGXCGESYPCW-UHFFFAOYSA-N alpha-phenylbenzeneacetic acid Natural products C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- UKXSKSHDVLQNKG-UHFFFAOYSA-N benzilic acid Chemical compound C=1C=CC=CC=1C(O)(C(=O)O)C1=CC=CC=C1 UKXSKSHDVLQNKG-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008918 emotional behaviour Effects 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid group Chemical class S(N)(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT53380/72A IT1052119B (it) | 1972-10-16 | 1972-10-16 | Derivati del triazolinone e procedimento per la loro preparazione |
| IT5338072 | 1972-10-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI58495B FI58495B (fi) | 1980-10-31 |
| FI58495C true FI58495C (fi) | 1981-02-10 |
Family
ID=11282276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI3188/73A FI58495C (fi) | 1972-10-16 | 1973-10-15 | Analogifoerfarande foer framstaellning av terapeutiskt aktiv 1-(3-(4-m-klorfenyl-1-piperazinyl)-propyl)-3,4-dietyl- 2-1,2,4-triazolin-5-on och farmaceutiskt godtagbara salter daerav |
Country Status (19)
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1047702B (it) * | 1975-07-24 | 1980-10-20 | Acraf | Nuova sintesi degli psicofarmaci denominati trazodone ed eteroperidone |
| IT1073639B (it) * | 1976-05-05 | 1985-04-17 | Acraf | Impiego del trazodone e etoperidone nel morbo di parikinson ed in altre sindromi extrapiramidali caratterizzate da tremori |
| US4162318A (en) * | 1976-05-05 | 1979-07-24 | Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. | Use of trazodone and etoperidone in Parkinsonism and in other extrapyramidal syndromes characterized by tremors |
| US4465683A (en) * | 1979-09-14 | 1984-08-14 | Mead Johnson & Company | Anti-psychotic agents |
| US4254124A (en) * | 1979-09-24 | 1981-03-03 | Mead Johnson & Company | Antidepressant agent |
| US4338317A (en) * | 1981-03-16 | 1982-07-06 | Mead Johnson & Company | Phenoxyethyl-1,2,4,-triazol-3-one antidepressants |
| US4487773A (en) * | 1981-03-16 | 1984-12-11 | Mead Johnson & Company | 1,2,4-Triazol-3-one antidepressants |
| US4367335A (en) * | 1981-08-03 | 1983-01-04 | Mead Johnson & Company | Thiazolidinylalkylene piperazine derivatives |
| US4386091A (en) * | 1982-02-24 | 1983-05-31 | Mead Johnson & Company | 2-Phenoxyalkyl-1,2,4-triazol-3-one antidepressants |
| US4575555A (en) * | 1983-06-29 | 1986-03-11 | Mead Johnson & Company | 4-(3-Chlorophenyl)-1,2,3,6-tetrahydropyridine derivative |
| US4613600A (en) * | 1983-09-30 | 1986-09-23 | Mead Johnson & Company | Antidepressant 1,2,4-triazolone compounds |
| US4784998A (en) * | 1987-04-06 | 1988-11-15 | Bristol-Myers Company | 1,3,4-oxadiazole pyschotropic compounds |
| US4931445A (en) * | 1988-10-06 | 1990-06-05 | Irwin Goldstein | Agents for treatment of male impotence |
| US5229406A (en) * | 1990-09-19 | 1993-07-20 | G. D. Searle & Co. | 1,3,5-trisubstituted-1,2,4-triazole compounds for treatment of circulatory disorders |
| US5140036A (en) * | 1990-09-19 | 1992-08-18 | G. D. Searle & Co. | 1,3,5-trisubstituted-1,2,4-triazole compounds for treatment of circulatory disorders |
| US5238952A (en) * | 1990-10-31 | 1993-08-24 | G. D. Searle & Co. | N-substituted imidazol-2-one compounds for treatment of circulatory disorders |
| US5087634A (en) * | 1990-10-31 | 1992-02-11 | G. D. Searle & Co. | N-substituted imidazol-2-one compounds for treatment of circulatory disorders |
| US5196537A (en) * | 1991-03-21 | 1993-03-23 | G. D. Searle & Co. | 5-apylheteroarylalkyl-1,3,5-trisubstituted-1,2,4-triazole compounds for treatment of circulatory disorders |
| US5164403A (en) * | 1991-04-05 | 1992-11-17 | G. D. Searle & Co. | N-arylheteroarylalkyl imidazol-2-one compounds for treatment of circulatory disorders |
| IT1256387B (it) * | 1992-11-13 | 1995-12-04 | Acraf | Procedimento per preparare triazoloni |
| CA2182241C (en) * | 1996-07-29 | 2002-09-17 | Bo Lei | Methods for the manufacture of nefazodone |
| ES2152860B1 (es) * | 1998-10-23 | 2001-08-16 | Finaf 92 Sa | Forma cristalina de la nefazodona y procedimiento para su preparacion. |
| WO2012072665A1 (en) | 2010-11-30 | 2012-06-07 | Pharmaneuroboost N.V. | Compositions comprising pipamperone and serotonin antagonist reuptake inhibitors |
-
1972
- 1972-10-16 IT IT53380/72A patent/IT1052119B/it active
-
1973
- 1973-01-01 AR AR250515A patent/AR204086A1/es active
- 1973-10-02 DK DK535473AA patent/DK141750B/da not_active IP Right Cessation
- 1973-10-03 CH CH1412473A patent/CH589643A5/xx not_active IP Right Cessation
- 1973-10-04 SE SE7313538A patent/SE390819B/xx unknown
- 1973-10-05 GB GB4654073A patent/GB1438337A/en not_active Expired
- 1973-10-08 YU YU2634/73A patent/YU39914B/xx unknown
- 1973-10-12 AT AT871173A patent/AT336021B/de not_active IP Right Cessation
- 1973-10-15 FI FI3188/73A patent/FI58495C/fi active
- 1973-10-15 CA CA183,407A patent/CA1013746A/en not_active Expired
- 1973-10-15 US US00406432A patent/US3857845A/en not_active Expired - Lifetime
- 1973-10-15 JP JP11565973A patent/JPS5550948B2/ja not_active Expired
- 1973-10-15 NO NO3987/73A patent/NO138565C/no unknown
- 1973-10-15 DE DE2351739A patent/DE2351739C3/de not_active Expired
- 1973-10-16 NL NLAANVRAGE7314204,A patent/NL184782C/xx not_active IP Right Cessation
- 1973-10-16 BE BE136751A patent/BE806146A/xx not_active IP Right Cessation
- 1973-10-16 FR FR7336853A patent/FR2202702B1/fr not_active Expired
- 1973-10-16 ES ES419687A patent/ES419687A1/es not_active Expired
-
1978
- 1978-03-08 KE KE2823A patent/KE2823A/xx unknown
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| DK170043B1 (da) | 5-phenyl-1,4,5,6-tetrahydropyrimidinderivater, fremgangsmåde til fremstilling heraf, farmaceutisk middel indeholdende disse samt anvendelse af derivaterne til fremstilling af et farmaceutisk middel | |
| CA2306428C (fr) | Derives de la 3-oxo-2(h)-1,2,4 - triazine en tant que ligands des recepteurs 5ht1a | |
| FI60863B (fi) | Foerfarande foer framstaellning av nya bentshydryloxialkylaminderivat med foerlaengd antihistamineffekt | |
| SU1736337A3 (ru) | Способ получени [ @ -(трет-бутиламинометил)-3,4-дихлорбензил]-тиоацетамида или его солей | |
| JPS584026B2 (ja) | ピラジンユウドウタイ オヨビ セイホウ | |
| FI69074C (fi) | Foerfarande foer framstaellning av som psykotropiskt medel anvaendbar karbazolderivat | |
| FI57403C (fi) | Foerfarande foer framstaellning av blodtryckssaenkande 2-substituerade-4-amino-6,7,8-trialkoxikinazoliner |