CS196359B2 - Process for preparing new derivatives of morpholine - Google Patents
Process for preparing new derivatives of morpholine Download PDFInfo
- Publication number
- CS196359B2 CS196359B2 CS772663A CS266377A CS196359B2 CS 196359 B2 CS196359 B2 CS 196359B2 CS 772663 A CS772663 A CS 772663A CS 266377 A CS266377 A CS 266377A CS 196359 B2 CS196359 B2 CS 196359B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- benzyl
- morpholine
- hydrogen
- formula
- oxo
- Prior art date
Links
- 150000002780 morpholines Chemical class 0.000 title claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical group 0.000 claims abstract description 3
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 3
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 3
- -1 C1-C4 alkyl radical Chemical group 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- GVWRZZNYCOTWNN-UHFFFAOYSA-N 4-benzyl-2-(chloromethyl)morpholine Chemical compound C1COC(CCl)CN1CC1=CC=CC=C1 GVWRZZNYCOTWNN-UHFFFAOYSA-N 0.000 claims description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 6
- 210000003169 central nervous system Anatomy 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- LHXCUWOJEALYLZ-BTJKTKAUSA-N (z)-but-2-enedioic acid;morpholine Chemical compound C1COCCN1.OC(=O)\C=C/C(O)=O LHXCUWOJEALYLZ-BTJKTKAUSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 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
- JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WTYBIAFPXBJWHO-UHFFFAOYSA-N 1-[(4-benzylmorpholin-2-yl)methyl]-5-chloro-3-phenylbenzimidazol-2-one;hydrochloride Chemical compound Cl.O=C1N(C=2C=CC=CC=2)C2=CC(Cl)=CC=C2N1CC(OCC1)CN1CC1=CC=CC=C1 WTYBIAFPXBJWHO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 2
- 229960004801 imipramine Drugs 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- BSMBZELQNMXCFU-UHFFFAOYSA-N 1-(morpholin-2-ylmethyl)-3-propan-2-ylbenzimidazol-2-one Chemical compound O=C1N(C(C)C)C2=CC=CC=C2N1CC1CNCCO1 BSMBZELQNMXCFU-UHFFFAOYSA-N 0.000 description 1
- BDDUQCPKNKNLDI-UHFFFAOYSA-N 1-[(4-benzylmorpholin-2-yl)methyl]-3-methylbenzimidazol-2-one;hydrochloride Chemical compound Cl.O=C1N(C)C2=CC=CC=C2N1CC(OCC1)CN1CC1=CC=CC=C1 BDDUQCPKNKNLDI-UHFFFAOYSA-N 0.000 description 1
- RBMMXFXXBOKFKI-UHFFFAOYSA-N 1-[(4-benzylmorpholin-2-yl)methyl]-3-phenylbenzimidazol-2-one Chemical compound C12=CC=CC=C2N(C=2C=CC=CC=2)C(=O)N1CC(OCC1)CN1CC1=CC=CC=C1 RBMMXFXXBOKFKI-UHFFFAOYSA-N 0.000 description 1
- MSJFLHDHZYXJKR-UHFFFAOYSA-N 1-[(4-benzylmorpholin-2-yl)methyl]-3-prop-1-en-2-ylbenzimidazol-2-one Chemical compound O=C1N(C(=C)C)C2=CC=CC=C2N1CC(OCC1)CN1CC1=CC=CC=C1 MSJFLHDHZYXJKR-UHFFFAOYSA-N 0.000 description 1
- QCMQLVDPKSUFDA-UHFFFAOYSA-N 1-methyl-3-(morpholin-2-ylmethyl)benzimidazol-2-one;hydrochloride Chemical compound Cl.O=C1N(C)C2=CC=CC=C2N1CC1CNCCO1 QCMQLVDPKSUFDA-UHFFFAOYSA-N 0.000 description 1
- SPIVPMWCISGVIN-UHFFFAOYSA-N 1-phenyl-3h-imidazo[4,5-b]pyridin-2-one Chemical compound O=C1NC2=NC=CC=C2N1C1=CC=CC=C1 SPIVPMWCISGVIN-UHFFFAOYSA-N 0.000 description 1
- BIOWIFFUGVQJPB-UHFFFAOYSA-N 3-[(4-benzylmorpholin-2-yl)methyl]-5-methoxy-1-methylbenzimidazol-2-one;hydrochloride Chemical compound Cl.C12=CC(OC)=CC=C2N(C)C(=O)N1CC(OCC1)CN1CC1=CC=CC=C1 BIOWIFFUGVQJPB-UHFFFAOYSA-N 0.000 description 1
- AUGPRLHZAOPVIR-UHFFFAOYSA-N 3-benzyl-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1CC1=CC=CC=C1 AUGPRLHZAOPVIR-UHFFFAOYSA-N 0.000 description 1
- PYEHNKXDXBNHQQ-UHFFFAOYSA-N 3-methyl-1h-benzimidazol-2-one Chemical compound C1=CC=C2N(C)C(O)=NC2=C1 PYEHNKXDXBNHQQ-UHFFFAOYSA-N 0.000 description 1
- NQNIMGRMJWPMIA-UHFFFAOYSA-N 4-benzyl-3-(2-chloroethyl)morpholine Chemical compound C(C1=CC=CC=C1)N1C(COCC1)CCCl NQNIMGRMJWPMIA-UHFFFAOYSA-N 0.000 description 1
- UCBSMOSFCAQPAI-UHFFFAOYSA-N 5-chloro-3-phenyl-1h-benzimidazol-2-one Chemical compound C12=CC(Cl)=CC=C2NC(=O)N1C1=CC=CC=C1 UCBSMOSFCAQPAI-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- BLGXFZZNTVWLAY-CCZXDCJGSA-N Yohimbine Natural products C1=CC=C2C(CCN3C[C@@H]4CC[C@@H](O)[C@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-CCZXDCJGSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- BLGXFZZNTVWLAY-UHFFFAOYSA-N beta-Yohimbin Natural products C1=CC=C2C(CCN3CC4CCC(O)C(C4CC33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- PIPZGJSEDRMUAW-VJDCAHTMSA-N hydron;methyl (1s,15r,18s,19r,20s)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;chloride Chemical compound Cl.C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 PIPZGJSEDRMUAW-VJDCAHTMSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229960000317 yohimbine Drugs 0.000 description 1
- GQDDNDAYOVNZPG-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C[C]2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3N=C21 GQDDNDAYOVNZPG-SCYLSFHTSA-N 0.000 description 1
- AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 description 1
- 229960000949 yohimbine hydrochloride Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB16235/76A GB1550656A (en) | 1976-04-22 | 1976-04-22 | Morpholine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS196359B2 true CS196359B2 (en) | 1980-03-31 |
Family
ID=10073639
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS772663A CS196359B2 (en) | 1976-04-22 | 1977-04-21 | Process for preparing new derivatives of morpholine |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4122175A (OSRAM) |
| JP (1) | JPS52151179A (OSRAM) |
| AR (1) | AR214314A1 (OSRAM) |
| AT (1) | AT347961B (OSRAM) |
| AU (1) | AU507294B2 (OSRAM) |
| BE (1) | BE853782A (OSRAM) |
| CA (1) | CA1072555A (OSRAM) |
| CH (1) | CH599204A5 (OSRAM) |
| CS (1) | CS196359B2 (OSRAM) |
| DD (1) | DD129910A5 (OSRAM) |
| DE (1) | DE2717439A1 (OSRAM) |
| DK (1) | DK145301C (OSRAM) |
| ES (1) | ES457996A1 (OSRAM) |
| FR (1) | FR2348923A1 (OSRAM) |
| GB (1) | GB1550656A (OSRAM) |
| GR (1) | GR61359B (OSRAM) |
| HU (1) | HU172654B (OSRAM) |
| NL (1) | NL7704279A (OSRAM) |
| NO (1) | NO145840C (OSRAM) |
| PT (1) | PT66443B (OSRAM) |
| SE (1) | SE7704584L (OSRAM) |
| SU (1) | SU686617A3 (OSRAM) |
| ZA (1) | ZA772394B (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9324018D0 (en) * | 1993-11-23 | 1994-01-12 | Merck Sharp & Dohme | Therapeutic agents |
-
1976
- 1976-04-22 GB GB16235/76A patent/GB1550656A/en not_active Expired
-
1977
- 1977-04-13 GR GR53210A patent/GR61359B/el unknown
- 1977-04-15 PT PT66443A patent/PT66443B/pt unknown
- 1977-04-19 NL NL7704279A patent/NL7704279A/xx not_active Application Discontinuation
- 1977-04-19 FR FR7711749A patent/FR2348923A1/fr active Granted
- 1977-04-19 AR AR267266A patent/AR214314A1/es active
- 1977-04-19 NO NO771346A patent/NO145840C/no unknown
- 1977-04-20 ES ES457996A patent/ES457996A1/es not_active Expired
- 1977-04-20 CH CH488177A patent/CH599204A5/xx not_active IP Right Cessation
- 1977-04-20 DD DD7700198510A patent/DD129910A5/xx unknown
- 1977-04-20 DE DE19772717439 patent/DE2717439A1/de not_active Withdrawn
- 1977-04-20 ZA ZA00772394A patent/ZA772394B/xx unknown
- 1977-04-21 DK DK175077A patent/DK145301C/da active
- 1977-04-21 BE BE2055847A patent/BE853782A/xx unknown
- 1977-04-21 AT AT277777A patent/AT347961B/de not_active IP Right Cessation
- 1977-04-21 AU AU24485/77A patent/AU507294B2/en not_active Expired
- 1977-04-21 SE SE7704584A patent/SE7704584L/ unknown
- 1977-04-21 US US05/789,674 patent/US4122175A/en not_active Expired - Lifetime
- 1977-04-21 CS CS772663A patent/CS196359B2/cs unknown
- 1977-04-21 JP JP4633377A patent/JPS52151179A/ja active Pending
- 1977-04-22 HU HU77HE734A patent/HU172654B/hu unknown
- 1977-04-22 SU SU772475095A patent/SU686617A3/ru active
- 1977-04-22 CA CA276,779A patent/CA1072555A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7704279A (nl) | 1977-10-25 |
| BE853782A (fr) | 1977-10-21 |
| PT66443A (fr) | 1977-05-01 |
| CA1072555A (en) | 1980-02-26 |
| CH599204A5 (OSRAM) | 1978-05-12 |
| DK145301C (da) | 1983-04-25 |
| GR61359B (en) | 1978-10-26 |
| NO145840C (no) | 1982-06-09 |
| SE7704584L (sv) | 1977-10-23 |
| DE2717439A1 (de) | 1977-11-03 |
| JPS52151179A (en) | 1977-12-15 |
| HU172654B (en) | 1977-11-28 |
| DD129910A5 (de) | 1978-02-15 |
| DK175077A (da) | 1977-10-23 |
| DK145301B (da) | 1982-10-25 |
| ZA772394B (en) | 1978-03-29 |
| AU507294B2 (en) | 1980-02-07 |
| ATA277777A (de) | 1978-06-15 |
| ES457996A1 (es) | 1978-02-01 |
| FR2348923A1 (fr) | 1977-11-18 |
| AU2448577A (en) | 1978-10-26 |
| GB1550656A (en) | 1979-08-15 |
| AR214314A1 (es) | 1979-05-31 |
| AT347961B (de) | 1979-01-25 |
| FR2348923B1 (OSRAM) | 1980-03-14 |
| NO771346L (no) | 1977-10-25 |
| NO145840B (no) | 1982-03-01 |
| PT66443B (fr) | 1978-09-22 |
| SU686617A3 (ru) | 1979-09-15 |
| US4122175A (en) | 1978-10-24 |
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