SU1240359A3 - Способ получени производных пирролидина - Google Patents
Способ получени производных пирролидина Download PDFInfo
- Publication number
- SU1240359A3 SU1240359A3 SU833673511A SU3673511A SU1240359A3 SU 1240359 A3 SU1240359 A3 SU 1240359A3 SU 833673511 A SU833673511 A SU 833673511A SU 3673511 A SU3673511 A SU 3673511A SU 1240359 A3 SU1240359 A3 SU 1240359A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- temperature
- kpa
- total volume
- crystals
- reduced pressure
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 5
- 150000003235 pyrrolidines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 11
- -1 -oxy Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 104
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 78
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 69
- 239000013078 crystal Substances 0.000 description 69
- 239000000243 solution Substances 0.000 description 52
- 239000000047 product Substances 0.000 description 49
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 48
- 238000001914 filtration Methods 0.000 description 47
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 44
- 229940072033 potash Drugs 0.000 description 44
- 235000015320 potassium carbonate Nutrition 0.000 description 44
- 239000000203 mixture Substances 0.000 description 30
- 239000000706 filtrate Substances 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 27
- 235000013311 vegetables Nutrition 0.000 description 26
- 238000003756 stirring Methods 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000001816 cooling Methods 0.000 description 24
- 239000007787 solid Substances 0.000 description 24
- 238000009835 boiling Methods 0.000 description 22
- 238000002844 melting Methods 0.000 description 20
- 230000008018 melting Effects 0.000 description 20
- 239000012043 crude product Substances 0.000 description 14
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 10
- 239000000725 suspension Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000006187 pill Substances 0.000 description 6
- 229960005333 tetrabenazine Drugs 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- WIKYUJGCLQQFNW-UHFFFAOYSA-N prochlorperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 WIKYUJGCLQQFNW-UHFFFAOYSA-N 0.000 description 4
- 229960003111 prochlorperazine Drugs 0.000 description 4
- 208000009132 Catalepsy Diseases 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-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
- 206010047853 Waxy flexibility Diseases 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 206010015995 Eyelid ptosis Diseases 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- DOZZESQBLWOEBQ-UHFFFAOYSA-N chlorohydrazine Chemical compound NNCl DOZZESQBLWOEBQ-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 201000003004 ptosis Diseases 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 235000012712 vegetable carbon Nutrition 0.000 description 2
- 239000004108 vegetable carbon Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- NYNZQNWKBKUAII-KBXCAEBGSA-N (3s)-n-[5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-3-hydroxypyrrolidine-1-carboxamide Chemical compound C1[C@@H](O)CCN1C(=O)NC1=C2N=C(N3[C@H](CCC3)C=3C(=CC=C(F)C=3)F)C=CN2N=C1 NYNZQNWKBKUAII-KBXCAEBGSA-N 0.000 description 1
- UGAQMGXCNYQXHP-UHFFFAOYSA-N 1-ethoxypyrrolidin-2-one Chemical compound CCON1CCCC1=O UGAQMGXCNYQXHP-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000003270 anti-cataleptic effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 230000002898 effect on depression Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 206010016256 fatigue Diseases 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 208000018299 prostration Diseases 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 210000001364 upper extremity Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
-
- 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
- C07D295/12—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 singly or doubly bound nitrogen atoms
- C07D295/135—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 singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Luminescent Compositions (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8220492A FR2537133A1 (fr) | 1982-12-07 | 1982-12-07 | Nouveaux derives de la (piperazinyl-1)-5 pyrrolidine, leur preparation et les medicaments qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1240359A3 true SU1240359A3 (ru) | 1986-06-23 |
Family
ID=9279863
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU833673511A SU1240359A3 (ru) | 1982-12-07 | 1983-12-06 | Способ получени производных пирролидина |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4547504A (enExample) |
| EP (1) | EP0110795B1 (enExample) |
| JP (1) | JPS59110670A (enExample) |
| AT (1) | ATE18548T1 (enExample) |
| AU (1) | AU560075B2 (enExample) |
| BG (1) | BG40808A3 (enExample) |
| CA (1) | CA1208645A (enExample) |
| CS (1) | CS240982B2 (enExample) |
| DD (1) | DD213216A5 (enExample) |
| DE (1) | DE3362566D1 (enExample) |
| DK (1) | DK562783A (enExample) |
| ES (1) | ES8406436A1 (enExample) |
| FI (1) | FI76320C (enExample) |
| FR (1) | FR2537133A1 (enExample) |
| GR (1) | GR72855B (enExample) |
| HU (1) | HU191903B (enExample) |
| IE (1) | IE56453B1 (enExample) |
| IL (1) | IL70396A (enExample) |
| MA (1) | MA19966A1 (enExample) |
| NO (1) | NO158218C (enExample) |
| NZ (1) | NZ206498A (enExample) |
| PL (1) | PL141385B1 (enExample) |
| PT (1) | PT77774B (enExample) |
| SU (1) | SU1240359A3 (enExample) |
| ZA (1) | ZA839070B (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2147583C1 (ru) * | 1989-05-19 | 2000-04-20 | Хехст-Рассел Фармасьютикалз Инкорпорейтед | Производные n-(арилоксиалкил)-гетероарилпиперидина и гетероарилпиперазина и фармацевтическая композиция на их основе |
| RU2163603C2 (ru) * | 1995-10-27 | 2001-02-27 | Грюненталь Гмбх | Замещенные имидазолидин-2,4-дионовые соединения в качестве фармацевтических действующих веществ |
| RU2199534C2 (ru) * | 1997-10-14 | 2003-02-27 | Мицубиси Фарма Корпорейшн | СОЕДИНЕНИЕ ПИПЕРАЗИНА, ИНГИБИТОР ПРОДУЦИРОВАНИЯ TNF-α И /ИЛИ ПРОМОТОР ПРОДУЦИРОВАНИЯ IL-10 И СРЕДСТВО ДЛЯ ПРОФИЛАКТИКИ ИЛИ ЛЕЧЕНИЯ БОЛЕЗНЕЙ НА ЕГО ОСНОВЕ |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK93087A (da) * | 1986-02-27 | 1987-08-28 | Duphar Int Res | Hidtil ukendte aryl substituerede (n-piperidinyl)methyl- og (n-piperazinyl)methylazoler med antipsykotiske egenskaber |
| US5066663A (en) * | 1990-05-21 | 1991-11-19 | Warner-Lambert Company | Substituted-hetero-cyclopentanones and cyclopentenones and derivatives thereof acting at muscarinic receptors |
| US6897213B1 (en) | 1995-11-21 | 2005-05-24 | Warner-Lambert Company | Heterocycles as cholecystokinin (CCK) ligands |
| US5969138A (en) * | 1996-11-01 | 1999-10-19 | Mitsui Chemicals, Inc. | Pyrrolidinone derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4247549A (en) * | 1978-12-27 | 1981-01-27 | Ici Americas Inc. | Piperazine-1-carboxylic acid esters possessing antidepressant or analgesic activity |
-
1982
- 1982-12-07 FR FR8220492A patent/FR2537133A1/fr active Granted
-
1983
- 1983-12-02 CS CS839041A patent/CS240982B2/cs unknown
- 1983-12-05 GR GR73154A patent/GR72855B/el unknown
- 1983-12-05 DD DD83257518A patent/DD213216A5/de unknown
- 1983-12-05 FI FI834453A patent/FI76320C/fi not_active IP Right Cessation
- 1983-12-05 PL PL1983244921A patent/PL141385B1/pl unknown
- 1983-12-06 US US06/558,775 patent/US4547504A/en not_active Expired - Fee Related
- 1983-12-06 MA MA20187A patent/MA19966A1/fr unknown
- 1983-12-06 DE DE8383402354T patent/DE3362566D1/de not_active Expired
- 1983-12-06 IE IE2867/83A patent/IE56453B1/xx unknown
- 1983-12-06 NZ NZ206498A patent/NZ206498A/en unknown
- 1983-12-06 DK DK562783A patent/DK562783A/da not_active Application Discontinuation
- 1983-12-06 HU HU834166A patent/HU191903B/hu unknown
- 1983-12-06 AU AU22108/83A patent/AU560075B2/en not_active Ceased
- 1983-12-06 AT AT83402354T patent/ATE18548T1/de not_active IP Right Cessation
- 1983-12-06 SU SU833673511A patent/SU1240359A3/ru active
- 1983-12-06 JP JP58229251A patent/JPS59110670A/ja active Pending
- 1983-12-06 IL IL70396A patent/IL70396A/xx not_active IP Right Cessation
- 1983-12-06 PT PT77774A patent/PT77774B/pt unknown
- 1983-12-06 ZA ZA839070A patent/ZA839070B/xx unknown
- 1983-12-06 EP EP83402354A patent/EP0110795B1/fr not_active Expired
- 1983-12-06 CA CA000442681A patent/CA1208645A/fr not_active Expired
- 1983-12-06 NO NO834481A patent/NO158218C/no unknown
- 1983-12-07 ES ES527897A patent/ES8406436A1/es not_active Expired
- 1983-12-07 BG BG063371A patent/BG40808A3/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| Патент US №4247549, кл. 424-250, опублик. 1981. * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2147583C1 (ru) * | 1989-05-19 | 2000-04-20 | Хехст-Рассел Фармасьютикалз Инкорпорейтед | Производные n-(арилоксиалкил)-гетероарилпиперидина и гетероарилпиперазина и фармацевтическая композиция на их основе |
| RU2239434C2 (ru) * | 1989-05-19 | 2004-11-10 | Авентис Фармасьютикалз Инк. | Производные n-(арилоксиалкил)-гетероарилпиперидина и -гетероарилпиперазина, промежуточные соединения и способ лечения психозов |
| RU2163603C2 (ru) * | 1995-10-27 | 2001-02-27 | Грюненталь Гмбх | Замещенные имидазолидин-2,4-дионовые соединения в качестве фармацевтических действующих веществ |
| RU2199534C2 (ru) * | 1997-10-14 | 2003-02-27 | Мицубиси Фарма Корпорейшн | СОЕДИНЕНИЕ ПИПЕРАЗИНА, ИНГИБИТОР ПРОДУЦИРОВАНИЯ TNF-α И /ИЛИ ПРОМОТОР ПРОДУЦИРОВАНИЯ IL-10 И СРЕДСТВО ДЛЯ ПРОФИЛАКТИКИ ИЛИ ЛЕЧЕНИЯ БОЛЕЗНЕЙ НА ЕГО ОСНОВЕ |
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