PT85944B - Processo para a preparacao de imidas biciclicas em ponte uteis como agentes ansioliticos e antidepressivos - Google Patents
Processo para a preparacao de imidas biciclicas em ponte uteis como agentes ansioliticos e antidepressivos Download PDFInfo
- Publication number
- PT85944B PT85944B PT85944A PT8594487A PT85944B PT 85944 B PT85944 B PT 85944B PT 85944 A PT85944 A PT 85944A PT 8594487 A PT8594487 A PT 8594487A PT 85944 B PT85944 B PT 85944B
- Authority
- PT
- Portugal
- Prior art keywords
- formula
- pyrimidinyl
- dione
- compound
- product
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 36
- 230000008569 process Effects 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title claims description 15
- 239000000935 antidepressant agent Substances 0.000 title description 8
- 150000003949 imides Chemical class 0.000 title description 3
- -1 bicyclic imide compounds Chemical class 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 56
- 150000003839 salts Chemical class 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- GJYXGIIWJFZCLN-UHFFFAOYSA-N octane-2,4-dione Chemical compound CCCCC(=O)CC(C)=O GJYXGIIWJFZCLN-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 150000008064 anhydrides Chemical class 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
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- 101150029512 SCG2 gene Proteins 0.000 claims 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 abstract description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 8
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- 208000024891 symptom Diseases 0.000 abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 4
- 125000005462 imide group Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 230000009102 absorption Effects 0.000 description 19
- 238000010521 absorption reaction Methods 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000001228 spectrum Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 239000002249 anxiolytic agent Substances 0.000 description 12
- 241000700159 Rattus Species 0.000 description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- YDQAUSHJSHIVAD-UHFFFAOYSA-N 4-(4-pyrimidin-2-ylpiperazin-1-yl)butan-1-amine Chemical compound C1CN(CCCCN)CCN1C1=NC=CC=N1 YDQAUSHJSHIVAD-UHFFFAOYSA-N 0.000 description 9
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- PRRYEPGBLHSBOL-UHFFFAOYSA-N oct-6-ene-2,4-dione Chemical compound CC=CCC(=O)CC(C)=O PRRYEPGBLHSBOL-UHFFFAOYSA-N 0.000 description 2
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- JRGGUPZKKTVKOV-UHFFFAOYSA-N 1-bromo-3-chlorobenzene Chemical compound ClC1=CC=CC(Br)=C1 JRGGUPZKKTVKOV-UHFFFAOYSA-N 0.000 description 1
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 1
- BTSFTGJOSYDDFX-UHFFFAOYSA-N 4-[4-(4-fluoropyrimidin-2-yl)piperazin-1-yl]butan-1-amine Chemical compound C1CN(CCCCN)CCN1C1=NC=CC(F)=N1 BTSFTGJOSYDDFX-UHFFFAOYSA-N 0.000 description 1
- NRQVXWNPFZZDMQ-UHFFFAOYSA-N 5,8,8-trimethyl-3-azabicyclo[3.2.1]octane-2,4-dione Chemical class O=C1NC(=O)C2(C)CCC1C2(C)C NRQVXWNPFZZDMQ-UHFFFAOYSA-N 0.000 description 1
- VFZDNKRDYPTSTP-UHFFFAOYSA-N 5,8,8-trimethyl-3-oxabicyclo[3.2.1]octane-2,4-dione Chemical compound O=C1OC(=O)C2(C)CCC1C2(C)C VFZDNKRDYPTSTP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000030090 Acute Disease Diseases 0.000 description 1
- 206010002869 Anxiety symptoms Diseases 0.000 description 1
- LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
- 208000017667 Chronic Disease Diseases 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- PXXNTAGJWPJAGM-VCOUNFBDSA-N Decaline Chemical compound C=1([C@@H]2C3)C=C(OC)C(OC)=CC=1OC(C=C1)=CC=C1CCC(=O)O[C@H]3C[C@H]1N2CCCC1 PXXNTAGJWPJAGM-VCOUNFBDSA-N 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229940123445 Tricyclic antidepressant Drugs 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
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- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- PXRIAVXPRVICRE-UHFFFAOYSA-N benzenesulfonic acid;4-methylbenzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1.CC1=CC=C(S(O)(=O)=O)C=C1 PXRIAVXPRVICRE-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- DSSYKIVIOFKYAU-UHFFFAOYSA-N camphor Chemical compound C1CC2(C)C(=O)CC1C2(C)C DSSYKIVIOFKYAU-UHFFFAOYSA-N 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
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- 238000007796 conventional method Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
- 229960004801 imipramine Drugs 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- MOODSJOROWROTO-UHFFFAOYSA-N salicylsulfuric acid Chemical compound OC(=O)C1=CC=CC=C1OS(O)(=O)=O MOODSJOROWROTO-UHFFFAOYSA-N 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 229940071103 sulfosalicylate Drugs 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1986/002224 WO1988003024A1 (en) | 1986-10-21 | 1986-10-21 | Bridged bicyclic imides as anxiolytics and antidepressants |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PT85944A PT85944A (en) | 1987-11-01 |
| PT85944B true PT85944B (pt) | 1990-07-31 |
Family
ID=22195680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT85944A PT85944B (pt) | 1986-10-21 | 1987-10-19 | Processo para a preparacao de imidas biciclicas em ponte uteis como agentes ansioliticos e antidepressivos |
Country Status (26)
| Country | Link |
|---|---|
| EP (1) | EP0268369B1 (en, 2012) |
| JP (1) | JPS63112581A (en, 2012) |
| KR (1) | KR900000565B1 (en, 2012) |
| CN (1) | CN1015987B (en, 2012) |
| AT (1) | ATE66222T1 (en, 2012) |
| AU (1) | AU579963B2 (en, 2012) |
| DD (1) | DD263531A5 (en, 2012) |
| DE (1) | DE3772158D1 (en, 2012) |
| DK (1) | DK547487A (en, 2012) |
| EG (1) | EG18718A (en, 2012) |
| ES (1) | ES2031517T3 (en, 2012) |
| FI (1) | FI90775C (en, 2012) |
| GR (1) | GR3002483T3 (en, 2012) |
| HU (1) | HU198203B (en, 2012) |
| IE (1) | IE60378B1 (en, 2012) |
| IL (1) | IL84206A (en, 2012) |
| MX (1) | MX8898A (en, 2012) |
| MY (1) | MY101833A (en, 2012) |
| NO (1) | NO882715L (en, 2012) |
| NZ (1) | NZ222229A (en, 2012) |
| PH (1) | PH23806A (en, 2012) |
| PL (1) | PL149172B1 (en, 2012) |
| PT (1) | PT85944B (en, 2012) |
| WO (1) | WO1988003024A1 (en, 2012) |
| YU (1) | YU45461B (en, 2012) |
| ZA (1) | ZA877863B (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4748240A (en) * | 1987-04-03 | 1988-05-31 | American Home Products Corporation | Psychotropic bicyclic imides |
| US4810789A (en) * | 1987-08-28 | 1989-03-07 | Bristol-Myers Company | Process for buspirone hydrochloride polymorphic crystalline form conversion |
| WO1990002552A1 (en) * | 1988-09-16 | 1990-03-22 | Pfizer Inc. | Antipsychotic 4-[4-(3-benzisothiazolyl)-1-piperazinyl]butyl bridged bicyclic imides |
| SU1825501A3 (ru) * | 1990-10-29 | 1995-12-10 | И.В. Комиссаров | Dl-3-[(4-[4- (2-пиридил)-1- пиперазинил]бутил)] -1,8,8-триметил -3-азабицикло[3,2,1] октан-2,4-диона дигидрохлорид, проявляющий противотревожную, нейролептическую и противорвотную активность |
| CN101906107B (zh) * | 2010-08-02 | 2012-12-26 | 南京林业大学 | 一种由α-蒎烯合成樟脑酸酐的方法 |
| HK1215170A1 (zh) | 2012-11-14 | 2016-08-19 | The Johns Hopkins University | 治療精神分裂症的方法和組合物 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4006233A (en) * | 1974-10-04 | 1977-02-01 | Merck & Co., Inc. | N-(pyrimidinyl)-tricyclo[3(or 4).2.2.02,4(or 5) ]-non (or dec)ene-dicarboximides |
| US4173646A (en) * | 1974-10-04 | 1979-11-06 | Merck & Co., Inc. | Tricyclicdicarboximides |
| US4182763A (en) * | 1978-05-22 | 1980-01-08 | Mead Johnson & Company | Buspirone anti-anxiety method |
| US4524206A (en) * | 1983-09-12 | 1985-06-18 | Mead Johnson & Company | 1-Heteroaryl-4-(2,5-pyrrolidinedion-1-yl)alkyl)piperazine derivatives |
| US4562255A (en) * | 1984-03-30 | 1985-12-31 | American Home Products Corporation | Substituted bi-alicyclic imides |
| JPS61238784A (ja) * | 1985-04-17 | 1986-10-24 | Sumitomo Seiyaku Kk | コハク酸イミド誘導体及びその酸付加塩 |
| DE3529872A1 (de) * | 1985-08-21 | 1987-02-26 | Kali Chemie Pharma Gmbh | Neue tetraoxoverbindungen |
-
1986
- 1986-10-19 DD DD86308077A patent/DD263531A5/de not_active IP Right Cessation
- 1986-10-21 MX MX889887A patent/MX8898A/es unknown
- 1986-10-21 HU HU865457A patent/HU198203B/hu not_active IP Right Cessation
- 1986-10-21 WO PCT/US1986/002224 patent/WO1988003024A1/en active IP Right Grant
-
1987
- 1987-01-21 IE IE283587A patent/IE60378B1/en not_active IP Right Cessation
- 1987-09-01 MY MYPI87001503A patent/MY101833A/en unknown
- 1987-10-13 ES ES198787309018T patent/ES2031517T3/es not_active Expired - Lifetime
- 1987-10-13 DE DE8787309018T patent/DE3772158D1/de not_active Expired - Lifetime
- 1987-10-13 AT AT87309018T patent/ATE66222T1/de not_active IP Right Cessation
- 1987-10-13 EP EP87309018A patent/EP0268369B1/en not_active Expired - Lifetime
- 1987-10-19 EG EG60187A patent/EG18718A/xx active
- 1987-10-19 PT PT85944A patent/PT85944B/pt unknown
- 1987-10-19 PH PH35953A patent/PH23806A/en unknown
- 1987-10-19 YU YU1920/87A patent/YU45461B/xx unknown
- 1987-10-19 IL IL84206A patent/IL84206A/xx not_active IP Right Cessation
- 1987-10-19 PL PL1987268296A patent/PL149172B1/pl unknown
- 1987-10-20 ZA ZA877863A patent/ZA877863B/xx unknown
- 1987-10-20 AU AU79946/87A patent/AU579963B2/en not_active Ceased
- 1987-10-20 KR KR1019870011634A patent/KR900000565B1/ko not_active Expired
- 1987-10-20 CN CN87107107A patent/CN1015987B/zh not_active Expired
- 1987-10-20 DK DK547487A patent/DK547487A/da not_active Application Discontinuation
- 1987-10-20 NZ NZ222229A patent/NZ222229A/xx unknown
- 1987-10-21 JP JP62266153A patent/JPS63112581A/ja active Granted
-
1988
- 1988-06-20 NO NO88882715A patent/NO882715L/no unknown
- 1988-06-20 FI FI882942A patent/FI90775C/fi not_active IP Right Cessation
-
1991
- 1991-08-16 GR GR91401123T patent/GR3002483T3/el unknown
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