PL82685B1 - Dibenzazepine derivatives and their preparation[ie34441b1] - Google Patents
Dibenzazepine derivatives and their preparation[ie34441b1] Download PDFInfo
- Publication number
- PL82685B1 PL82685B1 PL1970142553A PL14255370A PL82685B1 PL 82685 B1 PL82685 B1 PL 82685B1 PL 1970142553 A PL1970142553 A PL 1970142553A PL 14255370 A PL14255370 A PL 14255370A PL 82685 B1 PL82685 B1 PL 82685B1
- Authority
- PL
- Poland
- Prior art keywords
- compound
- alkyl
- reacting
- prepared
- formula
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 3
- LCGTWRLJTMHIQZ-UHFFFAOYSA-N 5H-dibenzo[b,f]azepine Chemical class C1=CC2=CC=CC=C2NC2=CC=CC=C21 LCGTWRLJTMHIQZ-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 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 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- QDOJMRUIKJJWEF-UHFFFAOYSA-N 3-chloro-11-methyl-5,6-dihydrobenzo[b][1]benzazepin-6-amine Chemical compound ClC1=CC2=C(N(C3=C(C(C2)N)C=CC=C3)C)C=C1 QDOJMRUIKJJWEF-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000935 antidepressant agent Substances 0.000 abstract description 2
- 229940005513 antidepressants Drugs 0.000 abstract description 2
- 150000002148 esters Chemical group 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 10
- 229910052799 carbon Inorganic materials 0.000 abstract 4
- 125000002252 acyl group Chemical group 0.000 abstract 3
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract 3
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 1
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000002082 anti-convulsion Effects 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- WCCYJYFGUQSEBB-UHFFFAOYSA-N ethyl N-(3-chloro-11-methyl-5,6-dihydrobenzo[b][1]benzazepin-6-yl)carbamate Chemical compound ClC1=CC2=C(N(C3=C(C(C2)NC(=O)OCC)C=CC=C3)C)C=C1 WCCYJYFGUQSEBB-UHFFFAOYSA-N 0.000 abstract 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 abstract 1
- 238000011200 topical administration Methods 0.000 abstract 1
- 230000002936 tranquilizing effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 239000012153 distilled water Substances 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 10
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 7
- 239000013078 crystal Substances 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 229910001023 sodium amalgam Inorganic materials 0.000 description 6
- 235000012712 vegetable carbon Nutrition 0.000 description 6
- 239000004108 vegetable carbon Substances 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000007900 aqueous suspension Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 229940098779 methanesulfonic acid Drugs 0.000 description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- -1 butanol Chemical compound 0.000 description 4
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 229910000497 Amalgam Inorganic materials 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 241001465754 Metazoa Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GZUDDYUDRYERRR-UHFFFAOYSA-N NC1=CC=CC=2NC3=C(CCC21)C=CC=C3 Chemical class NC1=CC=CC=2NC3=C(CCC21)C=CC=C3 GZUDDYUDRYERRR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 241001104043 Syringa Species 0.000 description 1
- 235000004338 Syringa vulgaris Nutrition 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N Theophylline Natural products O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 150000001538 azepines Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QFWACQSXKWRSLR-UHFFFAOYSA-N carboniodidic acid Chemical compound OC(I)=O QFWACQSXKWRSLR-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000005452 ethyl sulfates Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000011221 initial treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229940124641 pain reliever Drugs 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 235000021395 porridge Nutrition 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic 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
- 238000011282 treatment Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR6927226A FR2069831A1 (en, 2012) | 1969-08-07 | 1969-08-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL82685B1 true PL82685B1 (en) | 1975-10-31 |
Family
ID=9038789
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1970142553A PL82685B1 (en) | 1969-08-07 | 1970-08-06 | Dibenzazepine derivatives and their preparation[ie34441b1] |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS4939275B1 (en, 2012) |
| AT (2) | AT299211B (en, 2012) |
| BE (1) | BE754532A (en, 2012) |
| CH (1) | CH516560A (en, 2012) |
| CS (2) | CS163771B2 (en, 2012) |
| DE (2) | DE2039396A1 (en, 2012) |
| ES (2) | ES382564A1 (en, 2012) |
| FR (1) | FR2069831A1 (en, 2012) |
| GB (2) | GB1301366A (en, 2012) |
| IE (1) | IE34441B1 (en, 2012) |
| IL (1) | IL35070A0 (en, 2012) |
| LU (1) | LU61484A1 (en, 2012) |
| NL (1) | NL7011296A (en, 2012) |
| OA (1) | OA03651A (en, 2012) |
| PL (1) | PL82685B1 (en, 2012) |
| SU (2) | SU370777A3 (en, 2012) |
| ZA (1) | ZA705448B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2198942B1 (en, 2012) * | 1972-09-12 | 1975-03-14 | Rhone Poulenc Ind | |
| GB9518994D0 (en) * | 1995-09-16 | 1995-11-15 | Agrevo Uk Ltd | Fungicides |
| GB0415320D0 (en) * | 2004-07-08 | 2004-08-11 | Astrazeneca Ab | Novel compounds |
-
0
- BE BE754532D patent/BE754532A/xx unknown
-
1969
- 1969-08-07 FR FR6927226A patent/FR2069831A1/fr not_active Withdrawn
-
1970
- 1970-07-29 OA OA53994A patent/OA03651A/xx unknown
- 1970-07-30 NL NL7011296A patent/NL7011296A/xx unknown
- 1970-08-03 SU SU1466527A patent/SU370777A3/ru active
- 1970-08-03 SU SU1663229A patent/SU399124A3/ru active
- 1970-08-04 CS CS5442A patent/CS163771B2/cs unknown
- 1970-08-04 CS CS7446*A patent/CS163772B2/cs unknown
- 1970-08-06 LU LU61484D patent/LU61484A1/xx unknown
- 1970-08-06 IE IE1014/70A patent/IE34441B1/xx unknown
- 1970-08-06 PL PL1970142553A patent/PL82685B1/pl unknown
- 1970-08-06 IL IL35070A patent/IL35070A0/xx unknown
- 1970-08-06 ZA ZA705448A patent/ZA705448B/xx unknown
- 1970-08-06 CH CH1186870A patent/CH516560A/fr not_active IP Right Cessation
- 1970-08-07 ES ES382564A patent/ES382564A1/es not_active Expired
- 1970-08-07 GB GB1301366D patent/GB1301366A/en not_active Expired
- 1970-08-07 AT AT721170A patent/AT299211B/de not_active IP Right Cessation
- 1970-08-07 GB GB1301367D patent/GB1301367A/en not_active Expired
- 1970-08-07 DE DE19702039396 patent/DE2039396A1/de active Pending
- 1970-08-07 AT AT581571A patent/AT301556B/de not_active IP Right Cessation
- 1970-08-07 DE DE19702064879 patent/DE2064879A1/de active Pending
- 1970-09-04 ES ES383390A patent/ES383390A1/es not_active Expired
-
1971
- 1971-04-13 JP JP46022821A patent/JPS4939275B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| LU61484A1 (en, 2012) | 1971-07-15 |
| SU370777A3 (en, 2012) | 1973-02-15 |
| BE754532A (fr) | 1971-02-08 |
| OA03651A (fr) | 1971-12-24 |
| DE2064879A1 (en, 2012) | 1972-02-10 |
| FR2069831A1 (en, 2012) | 1971-09-10 |
| ZA705448B (en) | 1971-04-28 |
| SU399124A3 (en, 2012) | 1973-09-27 |
| CS163772B2 (en, 2012) | 1975-11-07 |
| ES382564A1 (es) | 1973-05-01 |
| CH516560A (fr) | 1971-12-15 |
| ES383390A1 (es) | 1973-02-16 |
| GB1301366A (en, 2012) | 1972-12-29 |
| CS163771B2 (en, 2012) | 1975-11-07 |
| AT301556B (de) | 1972-09-11 |
| IE34441L (en) | 1971-02-07 |
| IE34441B1 (en) | 1975-05-14 |
| NL7011296A (en, 2012) | 1971-02-09 |
| DE2039396A1 (de) | 1971-02-18 |
| AT299211B (de) | 1972-06-12 |
| JPS4939275B1 (en, 2012) | 1974-10-24 |
| GB1301367A (en, 2012) | 1972-12-29 |
| IL35070A0 (en) | 1970-10-30 |
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