SU707521A3 - Способ получени новых ди-или тетрагидробенз изоиндолинов или их изомеров или рацемических смесей этих оптических изомеров или их солей - Google Patents
Способ получени новых ди-или тетрагидробенз изоиндолинов или их изомеров или рацемических смесей этих оптических изомеров или их солейInfo
- Publication number
- SU707521A3 SU707521A3 SU762415454A SU2415454A SU707521A3 SU 707521 A3 SU707521 A3 SU 707521A3 SU 762415454 A SU762415454 A SU 762415454A SU 2415454 A SU2415454 A SU 2415454A SU 707521 A3 SU707521 A3 SU 707521A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- 9asr
- isoindoline
- tetrahydro
- over
- phenylbenz
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims 15
- 230000003287 optical effect Effects 0.000 title claims 6
- 238000000034 method Methods 0.000 title claims 5
- 150000003839 salts Chemical class 0.000 title claims 4
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 19
- 239000000243 solution Substances 0.000 claims 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 12
- 238000002425 crystallisation Methods 0.000 claims 10
- 230000008025 crystallization Effects 0.000 claims 9
- 239000007858 starting material Substances 0.000 claims 8
- 238000009835 boiling Methods 0.000 claims 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 238000010992 reflux Methods 0.000 claims 6
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 239000000741 silica gel Substances 0.000 claims 4
- 229910002027 silica gel Inorganic materials 0.000 claims 4
- -1 tin-amyl bromide Chemical compound 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 238000005804 alkylation reaction Methods 0.000 claims 3
- 229910052786 argon Inorganic materials 0.000 claims 3
- DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 claims 3
- 235000019253 formic acid Nutrition 0.000 claims 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- 238000007363 ring formation reaction Methods 0.000 claims 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- 230000029936 alkylation Effects 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims 2
- 238000000354 decomposition reaction Methods 0.000 claims 2
- USPLDBATMHXKKD-UHFFFAOYSA-N dichloromethane;pentane Chemical compound ClCCl.CCCCC USPLDBATMHXKKD-UHFFFAOYSA-N 0.000 claims 2
- 238000001704 evaporation Methods 0.000 claims 2
- 230000008020 evaporation Effects 0.000 claims 2
- 239000000284 extract Substances 0.000 claims 2
- 239000000706 filtrate Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims 2
- 238000002329 infrared spectrum Methods 0.000 claims 2
- 238000002844 melting Methods 0.000 claims 2
- 230000008018 melting Effects 0.000 claims 2
- 235000011121 sodium hydroxide Nutrition 0.000 claims 2
- UZLDZDGQEWRBAL-BZDVOYDHSA-N (2s)-2-[2-[[(2s)-1-hydroxybutan-2-yl]amino]ethylamino]butan-1-ol;[2-(pyridine-4-carbonyl)hydrazinyl]methanesulfonic acid Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO.OS(=O)(=O)CNNC(=O)C1=CC=NC=C1.OS(=O)(=O)CNNC(=O)C1=CC=NC=C1 UZLDZDGQEWRBAL-BZDVOYDHSA-N 0.000 claims 1
- LGUXJHPJBXZHDE-UHFFFAOYSA-N 1-(3-bromoprop-1-enyl)-3-chlorobenzene Chemical compound ClC1=CC=CC(C=CCBr)=C1 LGUXJHPJBXZHDE-UHFFFAOYSA-N 0.000 claims 1
- XPEHBUDGRZOFBP-UHFFFAOYSA-N 1-(3-bromoprop-1-enyl)-4-fluorobenzene Chemical compound FC1=CC=C(C=CCBr)C=C1 XPEHBUDGRZOFBP-UHFFFAOYSA-N 0.000 claims 1
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 claims 1
- JNVJIKKYWISIRR-UHFFFAOYSA-N 2,2,2-trifluoro-n-[3-(4-methylphenyl)prop-2-enyl]acetamide Chemical compound CC1=CC=C(C=CCNC(=O)C(F)(F)F)C=C1 JNVJIKKYWISIRR-UHFFFAOYSA-N 0.000 claims 1
- YCHBCAZCQRJJQZ-UHFFFAOYSA-N 2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]-3-(5-fluoro-1,3-dihydroisoindol-2-yl)propan-1-ol Chemical compound FC1=CC=C2C(C3CCN(CC3)C(CN3CC4=CC(F)=CC=C4C3)CO)=NOC2=C1 YCHBCAZCQRJJQZ-UHFFFAOYSA-N 0.000 claims 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims 1
- MJSHLKFJELZOSZ-UHFFFAOYSA-N 3-bromobut-1-enylbenzene Chemical compound CC(Br)C=CC1=CC=CC=C1 MJSHLKFJELZOSZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- VKJUUQBLVXUCCB-VOMDNODZSA-N 4-methyl-n,n-bis[(e)-3-phenylprop-2-enyl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N(C\C=C\C=1C=CC=CC=1)C\C=C\C1=CC=CC=C1 VKJUUQBLVXUCCB-VOMDNODZSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- KHKXHLDAAFZVKB-UHFFFAOYSA-N C(=O)=C1CC=C(C=C1)C1=CC=CC=C1 Chemical compound C(=O)=C1CC=C(C=C1)C1=CC=CC=C1 KHKXHLDAAFZVKB-UHFFFAOYSA-N 0.000 claims 1
- ZAGQNAMXHMNYJR-NTUHNPAUSA-N C(\C=C\C1=CC=CC=C1)N(C(C(F)(F)F)=O)CC#CC1=CC=CC=C1 Chemical compound C(\C=C\C1=CC=CC=C1)N(C(C(F)(F)F)=O)CC#CC1=CC=CC=C1 ZAGQNAMXHMNYJR-NTUHNPAUSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- MWHHJYUHCZWSLS-UHFFFAOYSA-N FC=1C=C(C=CC1C1=C2CNC(C2=C(C=C1)C=1NC(=CN1)C)=O)NC(=O)NC1=C(C=C(C=C1F)F)F Chemical compound FC=1C=C(C=CC1C1=C2CNC(C2=C(C=C1)C=1NC(=CN1)C)=O)NC(=O)NC1=C(C=C(C=C1F)F)F MWHHJYUHCZWSLS-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 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 claims 1
- 238000007126 N-alkylation reaction Methods 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000012300 argon atmosphere Substances 0.000 claims 1
- 239000012298 atmosphere Substances 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims 1
- WUEXFSVOXPGVML-UHFFFAOYSA-N ethanol;pentane Chemical compound CCO.CCCCC WUEXFSVOXPGVML-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 1
- 238000001640 fractional crystallisation Methods 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 150000002518 isoindoles Chemical class 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 229940050176 methyl chloride Drugs 0.000 claims 1
- 239000012299 nitrogen atmosphere Substances 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000012074 organic phase Substances 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000002002 slurry Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 229910052938 sodium sulfate Inorganic materials 0.000 claims 1
- 235000011152 sodium sulphate Nutrition 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- 230000017105 transposition Effects 0.000 claims 1
- KMIOJWCYOHBUJS-HAKPAVFJSA-N vorolanib Chemical compound C1N(C(=O)N(C)C)CC[C@@H]1NC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C KMIOJWCYOHBUJS-HAKPAVFJSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/62—Naphtho [c] pyrroles; Hydrogenated naphtho [c] pyrroles
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1425072A CH590231A5 (en) | 1972-09-29 | 1972-09-29 | Benzo(f)isoindoline derivs - with antidepressant and analgesic activity |
| CH1130573A CH605748A5 (en) | 1973-08-03 | 1973-08-03 | Benzo(f)isoindoline derivs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU707521A3 true SU707521A3 (ru) | 1979-12-30 |
Family
ID=25708104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762415454A SU707521A3 (ru) | 1972-09-29 | 1976-10-28 | Способ получени новых ди-или тетрагидробенз изоиндолинов или их изомеров или рацемических смесей этих оптических изомеров или их солей |
Country Status (18)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA003302B1 (ru) * | 1999-03-26 | 2003-04-24 | Ле Лаборатуар Сервье | ПРОИЗВОДНЫЕ БЕНЗО[3,4] ЦИКЛОБУТА [1,2-c] ПИРРОЛА И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ ИНГИБИТОРОВ ОБРАТНОГО ЗАХВАТА СЕРОТОНИНА |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2860878D1 (en) * | 1977-06-28 | 1981-10-29 | Sandoz Ag | New benz(f)isoindolines, their preparation and medicaments containing them |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE792374A (fr) * | 1971-12-08 | 1973-06-06 | Allen & Hanburys Ltd | Nouveaux derives d'isoindoline |
-
1973
- 1973-09-20 FI FI2934/73A patent/FI57748C/fi active
- 1973-09-20 DK DK516373AA patent/DK136420B/da not_active IP Right Cessation
- 1973-09-21 SE SE7312916A patent/SE394110B/xx unknown
- 1973-09-24 NL NL7313111A patent/NL7313111A/xx not_active Application Discontinuation
- 1973-09-26 DD DD173691A patent/DD114604A5/xx unknown
- 1973-09-26 DD DD187137*A patent/DD118630A5/xx unknown
- 1973-09-26 IL IL43333A patent/IL43333A/xx unknown
- 1973-09-27 IE IE1730/73A patent/IE39474B1/xx unknown
- 1973-09-27 DE DE19732348593 patent/DE2348593A1/de not_active Withdrawn
- 1973-09-28 AT AT833873A patent/AT339891B/de not_active IP Right Cessation
- 1973-09-28 GB GB4547773A patent/GB1449159A/en not_active Expired
- 1973-09-28 CA CA182,178A patent/CA1008865A/en not_active Expired
- 1973-09-28 JP JP48108577A patent/JPS602304B2/ja not_active Expired
- 1973-09-28 FR FR7334863A patent/FR2201092B1/fr not_active Expired
- 1973-09-29 ES ES419195A patent/ES419195A1/es not_active Expired
- 1973-10-01 PH PH15069A patent/PH12933A/en unknown
-
1975
- 1975-12-16 ES ES443519A patent/ES443519A1/es not_active Expired
- 1975-12-16 ES ES443517A patent/ES443517A1/es not_active Expired
- 1975-12-16 ES ES443518A patent/ES443518A1/es not_active Expired
-
1976
- 1976-10-28 SU SU762415454A patent/SU707521A3/ru active
-
1980
- 1980-01-03 HK HK3/80A patent/HK380A/xx unknown
- 1980-12-30 MY MY220/80A patent/MY8000220A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA003302B1 (ru) * | 1999-03-26 | 2003-04-24 | Ле Лаборатуар Сервье | ПРОИЗВОДНЫЕ БЕНЗО[3,4] ЦИКЛОБУТА [1,2-c] ПИРРОЛА И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ ИНГИБИТОРОВ ОБРАТНОГО ЗАХВАТА СЕРОТОНИНА |
Also Published As
| Publication number | Publication date |
|---|---|
| DD114604A5 (enrdf_load_stackoverflow) | 1975-08-12 |
| DK136420C (enrdf_load_stackoverflow) | 1978-03-13 |
| JPS4970960A (enrdf_load_stackoverflow) | 1974-07-09 |
| MY8000220A (en) | 1980-12-31 |
| SE394110B (sv) | 1977-06-06 |
| DE2348593A1 (de) | 1974-04-11 |
| JPS602304B2 (ja) | 1985-01-21 |
| IL43333A0 (en) | 1973-11-28 |
| IE39474B1 (en) | 1978-10-25 |
| FR2201092A1 (enrdf_load_stackoverflow) | 1974-04-26 |
| DK136420B (da) | 1977-10-10 |
| FI57748C (fi) | 1980-10-10 |
| HK380A (en) | 1980-01-11 |
| ES443518A1 (es) | 1977-08-01 |
| FR2201092B1 (enrdf_load_stackoverflow) | 1977-09-09 |
| ES443519A1 (es) | 1977-08-16 |
| PH12933A (en) | 1979-10-17 |
| AT339891B (de) | 1977-11-10 |
| FI57748B (fi) | 1980-06-30 |
| CA1008865A (en) | 1977-04-19 |
| ES443517A1 (es) | 1977-08-16 |
| IE39474L (en) | 1974-03-29 |
| NL7313111A (enrdf_load_stackoverflow) | 1974-04-02 |
| IL43333A (en) | 1978-10-31 |
| ATA833873A (de) | 1977-02-15 |
| GB1449159A (en) | 1976-09-15 |
| AU6085273A (en) | 1975-04-10 |
| ES419195A1 (es) | 1976-12-16 |
| DD118630A5 (enrdf_load_stackoverflow) | 1976-03-12 |
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