SU703021A3 - Способ получени двузамещенных пиперазинов или их солей - Google Patents
Способ получени двузамещенных пиперазинов или их солейInfo
- Publication number
- SU703021A3 SU703021A3 SU772558955A SU2558955A SU703021A3 SU 703021 A3 SU703021 A3 SU 703021A3 SU 772558955 A SU772558955 A SU 772558955A SU 2558955 A SU2558955 A SU 2558955A SU 703021 A3 SU703021 A3 SU 703021A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- piperazine
- thiadiazolyl
- methyl
- chloride
- piperonyl
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims 7
- 238000000034 method Methods 0.000 title claims 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 16
- -1 hydrochloric Chemical class 0.000 claims 8
- DWSUJONSJJTODA-UHFFFAOYSA-N 5-(chloromethyl)-1,3-benzodioxole Chemical compound ClCC1=CC=C2OCOC2=C1 DWSUJONSJJTODA-UHFFFAOYSA-N 0.000 claims 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- HARUWJZORCBAAL-UHFFFAOYSA-N 6-(chloromethyl)-2,3-dihydro-1,4-benzodioxine Chemical compound O1CCOC2=CC(CCl)=CC=C21 HARUWJZORCBAAL-UHFFFAOYSA-N 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 150000007513 acids Chemical class 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 238000004811 liquid chromatography Methods 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 238000002425 crystallisation Methods 0.000 claims 2
- 230000008025 crystallization Effects 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- WEYVCQFUGFRXOM-UHFFFAOYSA-N perazine Chemical compound C1CN(C)CCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 WEYVCQFUGFRXOM-UHFFFAOYSA-N 0.000 claims 2
- 229960002195 perazine Drugs 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 claims 1
- RUHJZSZTSCSTCC-UHFFFAOYSA-N 2-(bromomethyl)naphthalene Chemical compound C1=CC=CC2=CC(CBr)=CC=C21 RUHJZSZTSCSTCC-UHFFFAOYSA-N 0.000 claims 1
- VYFHMNIBSWVKIH-UHFFFAOYSA-N 5-chlorochromen-2-one Chemical compound O1C(=O)C=CC2=C1C=CC=C2Cl VYFHMNIBSWVKIH-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- DUMDXWLPYQNUCN-UHFFFAOYSA-N C1=CC(=C2C=CC(=O)OC2=C1)CCl Chemical compound C1=CC(=C2C=CC(=O)OC2=C1)CCl DUMDXWLPYQNUCN-UHFFFAOYSA-N 0.000 claims 1
- 239000004726 Luranyl Substances 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000003943 azolyl group Chemical group 0.000 claims 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 239000003518 caustics Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 238000002474 experimental method Methods 0.000 claims 1
- 238000005755 formation reaction Methods 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 239000012044 organic layer Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 235000011007 phosphoric acid Nutrition 0.000 claims 1
- 150000003016 phosphoric acids Chemical class 0.000 claims 1
- 238000000053 physical method Methods 0.000 claims 1
- 150000004885 piperazines Chemical class 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 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 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 238000012421 spiking Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- 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
-
- 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
- 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
- C07D249/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB54398/76A GB1560084A (en) | 1976-12-31 | 1976-12-31 | Disubstituted piperazines processes for their preparation and pharmaceutical mompositions containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU703021A3 true SU703021A3 (ru) | 1979-12-05 |
Family
ID=10470884
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772558955A SU703021A3 (ru) | 1976-12-31 | 1977-12-27 | Способ получени двузамещенных пиперазинов или их солей |
| SU782699397A SU793397A3 (ru) | 1976-12-31 | 1978-12-21 | Способ получени производных пиперазина или их солей |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782699397A SU793397A3 (ru) | 1976-12-31 | 1978-12-21 | Способ получени производных пиперазина или их солей |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4177272A (enExample) |
| JP (1) | JPS5384984A (enExample) |
| AR (3) | AR216931A1 (enExample) |
| AT (1) | AT358591B (enExample) |
| AU (1) | AU513087B2 (enExample) |
| BE (1) | BE862568A (enExample) |
| CA (1) | CA1100968A (enExample) |
| DD (1) | DD133802A5 (enExample) |
| DE (1) | DE2758314A1 (enExample) |
| DK (1) | DK572977A (enExample) |
| FR (1) | FR2376148A1 (enExample) |
| GB (1) | GB1560084A (enExample) |
| GR (1) | GR62407B (enExample) |
| IE (1) | IE46284B1 (enExample) |
| IL (1) | IL53714A (enExample) |
| NL (1) | NL7714628A (enExample) |
| NZ (1) | NZ186158A (enExample) |
| OA (1) | OA05840A (enExample) |
| PH (1) | PH14321A (enExample) |
| PT (1) | PT67486B (enExample) |
| SE (1) | SE7714884L (enExample) |
| SU (2) | SU703021A3 (enExample) |
| YU (1) | YU304377A (enExample) |
| ZA (1) | ZA777680B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2216545C2 (ru) * | 1993-10-28 | 2003-11-20 | Авентис Фармасьютикалз Инк. | Гетероарил-1-пиперидины и пиперазины, фармацевтическая композиция на их основе, способ лечения психозов и ослабления боли |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2418798A1 (fr) * | 1978-03-03 | 1979-09-28 | Science Union & Cie | Nouvelles piperazines disubstituees, leurs procedes de preparation et les compositions pharmaceutiques les renfermant |
| US4421753A (en) * | 1982-01-15 | 1983-12-20 | American Cyanamid Company | 1-(5-Amino-4H-1,2,4-triazol-3-yl)-4-substituted-piperazines |
| FR2519986A1 (fr) * | 1982-01-21 | 1983-07-22 | Adir | Nouveaux derives de benzodioxine, leurs procedes de preparation et les compositions pharmaceutiques les renfermant |
| US5637592A (en) * | 1994-07-12 | 1997-06-10 | Janssen Pharmaceutica N.V. | Acyl derivatives of azolones |
| FR2799464B1 (fr) * | 1999-10-12 | 2001-12-28 | Norchim | Procede de fabrication de piperonyl piperazine par animation reductive |
| EP3119774A1 (en) * | 2014-03-17 | 2017-01-25 | reMynd NV | Oxadiazole compounds |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1595923A1 (de) * | 1965-02-20 | 1969-11-27 | Merck Ag E | 1-Aralkyl-4-(thiazolyl-2)-piperazine und Verfahren zu ihrer Herstellung |
| GB1307256A (en) * | 1970-09-15 | 1973-02-14 | Science Union & Cie | Piperazine derivatives and a process for their preparation |
| GB1369379A (en) * | 1972-04-07 | 1974-10-09 | Science Union & Cie | Benzodioxole derivatives and processes for preparing them |
| GB1407552A (en) * | 1973-04-02 | 1975-09-24 | Science Union & Cie | Disubstituted piperazines processes for their preparation and pharmaceutical compositions containing them |
-
1976
- 1976-12-31 GB GB54398/76A patent/GB1560084A/en not_active Expired
-
1977
- 1977-12-21 IE IE2597/77A patent/IE46284B1/en unknown
- 1977-12-22 YU YU03043/77A patent/YU304377A/xx unknown
- 1977-12-22 DK DK572977A patent/DK572977A/da not_active Application Discontinuation
- 1977-12-22 CA CA293,755A patent/CA1100968A/fr not_active Expired
- 1977-12-22 FR FR7738727A patent/FR2376148A1/fr active Granted
- 1977-12-23 AT AT927577A patent/AT358591B/de not_active IP Right Cessation
- 1977-12-24 OA OA56358A patent/OA05840A/xx unknown
- 1977-12-27 US US05/864,204 patent/US4177272A/en not_active Expired - Lifetime
- 1977-12-27 JP JP15854677A patent/JPS5384984A/ja active Granted
- 1977-12-27 DE DE19772758314 patent/DE2758314A1/de not_active Ceased
- 1977-12-27 SU SU772558955A patent/SU703021A3/ru active
- 1977-12-28 ZA ZA00777680A patent/ZA777680B/xx unknown
- 1977-12-29 AR AR270568A patent/AR216931A1/es active
- 1977-12-29 AU AU32045/77A patent/AU513087B2/en not_active Expired
- 1977-12-29 PH PH20605A patent/PH14321A/en unknown
- 1977-12-29 SE SE7714884A patent/SE7714884L/xx unknown
- 1977-12-29 GR GR55066A patent/GR62407B/el unknown
- 1977-12-29 IL IL53714A patent/IL53714A/xx unknown
- 1977-12-30 DD DD7700203032A patent/DD133802A5/xx unknown
- 1977-12-30 PT PT67486A patent/PT67486B/pt unknown
- 1977-12-30 BE BE184051A patent/BE862568A/xx unknown
- 1977-12-31 NL NL7714628A patent/NL7714628A/xx not_active Application Discontinuation
-
1978
- 1978-01-05 NZ NZ186158A patent/NZ186158A/xx unknown
- 1978-12-21 SU SU782699397A patent/SU793397A3/ru active
-
1979
- 1979-02-27 AR AR275635A patent/AR217144A1/es active
- 1979-02-27 AR AR275634A patent/AR217143A1/es active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2216545C2 (ru) * | 1993-10-28 | 2003-11-20 | Авентис Фармасьютикалз Инк. | Гетероарил-1-пиперидины и пиперазины, фармацевтическая композиция на их основе, способ лечения психозов и ослабления боли |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5384984A (en) | 1978-07-26 |
| AU513087B2 (en) | 1980-11-13 |
| AT358591B (de) | 1980-09-25 |
| DE2758314A1 (de) | 1978-07-06 |
| ATA927577A (de) | 1980-02-15 |
| GR62407B (en) | 1979-04-11 |
| IE46284L (en) | 1978-06-30 |
| DK572977A (da) | 1978-07-01 |
| YU304377A (en) | 1983-01-21 |
| IL53714A (en) | 1981-07-31 |
| US4177272A (en) | 1979-12-04 |
| SE7714884L (sv) | 1978-07-02 |
| IE46284B1 (en) | 1983-04-20 |
| SU793397A3 (ru) | 1980-12-30 |
| IL53714A0 (en) | 1978-03-10 |
| JPS6149314B2 (enExample) | 1986-10-29 |
| PH14321A (en) | 1981-05-27 |
| CA1100968A (fr) | 1981-05-12 |
| PT67486B (fr) | 1979-05-30 |
| NL7714628A (nl) | 1978-07-04 |
| NZ186158A (en) | 1980-03-05 |
| FR2376148B1 (enExample) | 1981-05-29 |
| AR216931A1 (es) | 1980-02-15 |
| GB1560084A (en) | 1980-01-30 |
| ZA777680B (en) | 1978-10-25 |
| BE862568A (fr) | 1978-06-30 |
| AU3204577A (en) | 1979-07-05 |
| AR217144A1 (es) | 1980-02-29 |
| FR2376148A1 (fr) | 1978-07-28 |
| DD133802A5 (de) | 1979-01-24 |
| PT67486A (fr) | 1978-01-01 |
| OA05840A (fr) | 1981-05-31 |
| AR217143A1 (es) | 1980-02-29 |
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