NL8003674A - Nieuwe organische verbindingen, hun bereiding en far- maceutische preparaten, die deze verbindingen bevatten. - Google Patents
Nieuwe organische verbindingen, hun bereiding en far- maceutische preparaten, die deze verbindingen bevatten. Download PDFInfo
- Publication number
- NL8003674A NL8003674A NL8003674A NL8003674A NL8003674A NL 8003674 A NL8003674 A NL 8003674A NL 8003674 A NL8003674 A NL 8003674A NL 8003674 A NL8003674 A NL 8003674A NL 8003674 A NL8003674 A NL 8003674A
- Authority
- NL
- Netherlands
- Prior art keywords
- compounds
- carbon atoms
- hydrogen
- formula
- alkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 45
- 238000002360 preparation method Methods 0.000 title description 8
- 150000002894 organic compounds Chemical class 0.000 title description 2
- 239000000825 pharmaceutical preparation Substances 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 4
- -1 boron hydride compound Chemical class 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- XZNGTBLWFCRXKR-UHFFFAOYSA-N 3-phenyl-1h-indole Chemical compound C=1NC2=CC=CC=C2C=1C1=CC=CC=C1 XZNGTBLWFCRXKR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- HPOFFVSQUVOVLB-UHFFFAOYSA-N 1-(3-phenylindol-1-yl)propan-2-amine Chemical compound NC(CN1C=C(C2=CC=CC=C12)C1=CC=CC=C1)C HPOFFVSQUVOVLB-UHFFFAOYSA-N 0.000 description 2
- CIHQTLQBPSMKQB-UHFFFAOYSA-N 2-(3-phenylindol-1-yl)acetamide Chemical compound C12=CC=CC=C2N(CC(=O)N)C=C1C1=CC=CC=C1 CIHQTLQBPSMKQB-UHFFFAOYSA-N 0.000 description 2
- PXAHSPHLHQTNEL-UHFFFAOYSA-N 2-amino-1-(3-phenylindol-1-yl)propan-1-one Chemical compound NC(C(=O)N1C=C(C2=CC=CC=C12)C1=CC=CC=C1)C PXAHSPHLHQTNEL-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 229910010277 boron hydride Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- HCAJEUSONLESMK-UHFFFAOYSA-M cyclohexylsulfamate Chemical compound [O-]S(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-M 0.000 description 2
- ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WYXJKSZLZXVXOL-UHFFFAOYSA-N 1-(3-phenyl-2,3-dihydroindol-1-yl)propan-2-amine Chemical compound NC(CN1CC(C2=CC=CC=C12)C1=CC=CC=C1)C WYXJKSZLZXVXOL-UHFFFAOYSA-N 0.000 description 1
- IJRJQYHGWPIFLR-UHFFFAOYSA-N 2-(3-phenylindol-1-yl)ethanamine Chemical compound C12=CC=CC=C2N(CCN)C=C1C1=CC=CC=C1 IJRJQYHGWPIFLR-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- FDVYZESLXJSPHA-UHFFFAOYSA-N 3-(3-phenyl-2,3-dihydroindol-1-yl)propan-1-amine Chemical compound NCCCN1CC(C2=CC=CC=C12)C1=CC=CC=C1 FDVYZESLXJSPHA-UHFFFAOYSA-N 0.000 description 1
- AUOYENVGLJJZNS-UHFFFAOYSA-N 3-(3-phenylindol-1-yl)propan-1-amine Chemical compound C12=CC=CC=C2N(CCCN)C=C1C1=CC=CC=C1 AUOYENVGLJJZNS-UHFFFAOYSA-N 0.000 description 1
- IYDAOALWDSYCOA-UHFFFAOYSA-N 3-(3-phenylindol-1-yl)propanenitrile Chemical compound C12=CC=CC=C2N(CCC#N)C=C1C1=CC=CC=C1 IYDAOALWDSYCOA-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- KMHZPJNVPCAUMN-UHFFFAOYSA-N Erbon Chemical compound CC(Cl)(Cl)C(=O)OCCOC1=CC(Cl)=C(Cl)C=C1Cl KMHZPJNVPCAUMN-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 230000002903 catalepsic effect Effects 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- ROBXZHNBBCHEIQ-UHFFFAOYSA-N ethyl 2-aminopropanoate Chemical compound CCOC(=O)C(C)N ROBXZHNBBCHEIQ-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000003746 feather Anatomy 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000010575 fractional recrystallization Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960005333 tetrabenazine Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
-
- 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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH609879 | 1979-06-29 | ||
| CH609879 | 1979-06-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8003674A true NL8003674A (nl) | 1980-12-31 |
Family
ID=4304237
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8003674A NL8003674A (nl) | 1979-06-29 | 1980-06-25 | Nieuwe organische verbindingen, hun bereiding en far- maceutische preparaten, die deze verbindingen bevatten. |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS568363A (en, 2012) |
| AU (1) | AU5973980A (en, 2012) |
| BE (1) | BE884013A (en, 2012) |
| CA (1) | CA1134370A (en, 2012) |
| DE (1) | DE3022648A1 (en, 2012) |
| DK (1) | DK280380A (en, 2012) |
| ES (1) | ES492884A0 (en, 2012) |
| FI (1) | FI802002A7 (en, 2012) |
| FR (2) | FR2460296A1 (en, 2012) |
| GB (1) | GB2051811B (en, 2012) |
| IL (1) | IL60420A (en, 2012) |
| IT (1) | IT8049093A0 (en, 2012) |
| NL (1) | NL8003674A (en, 2012) |
| PT (1) | PT71465B (en, 2012) |
| SE (1) | SE8004757L (en, 2012) |
| ZA (1) | ZA803888B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW270114B (en, 2012) * | 1993-10-22 | 1996-02-11 | Hoffmann La Roche | |
| US6265403B1 (en) * | 1999-01-20 | 2001-07-24 | Merck & Co., Inc. | Angiogenesis inhibitors |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK96884C (da) * | 1959-09-14 | 1963-09-16 | Dumex Ltd As | Fremgangsmåde til fremstilling af indolderivater eller salte heraf. |
| US4080330A (en) * | 1975-06-23 | 1978-03-21 | Delmar Chemicals Limited | Phenylindolines and process for their production |
-
1980
- 1980-06-18 DE DE19803022648 patent/DE3022648A1/de not_active Withdrawn
- 1980-06-23 FI FI802002A patent/FI802002A7/fi not_active Application Discontinuation
- 1980-06-25 NL NL8003674A patent/NL8003674A/nl not_active Application Discontinuation
- 1980-06-25 GB GB8020753A patent/GB2051811B/en not_active Expired
- 1980-06-26 BE BE1/9865A patent/BE884013A/fr not_active IP Right Cessation
- 1980-06-27 DK DK280380A patent/DK280380A/da not_active Application Discontinuation
- 1980-06-27 ES ES492884A patent/ES492884A0/es active Granted
- 1980-06-27 PT PT71465A patent/PT71465B/pt unknown
- 1980-06-27 IL IL60420A patent/IL60420A/xx unknown
- 1980-06-27 ZA ZA00803888A patent/ZA803888B/xx unknown
- 1980-06-27 IT IT8049093A patent/IT8049093A0/it unknown
- 1980-06-27 AU AU59739/80A patent/AU5973980A/en not_active Abandoned
- 1980-06-27 SE SE8004757A patent/SE8004757L/xx not_active Application Discontinuation
- 1980-06-27 FR FR8014348A patent/FR2460296A1/fr active Granted
- 1980-06-27 CA CA000354967A patent/CA1134370A/en not_active Expired
- 1980-06-28 JP JP8845180A patent/JPS568363A/ja active Pending
-
1982
- 1982-11-08 FR FR8218841A patent/FR2514352A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| ES8105284A1 (es) | 1981-06-01 |
| PT71465B (fr) | 1981-07-03 |
| PT71465A (fr) | 1980-07-01 |
| IL60420A (en) | 1983-10-31 |
| SE8004757L (sv) | 1980-12-30 |
| DE3022648A1 (de) | 1981-01-15 |
| FR2460296B1 (en, 2012) | 1983-08-05 |
| AU5973980A (en) | 1981-01-08 |
| GB2051811A (en) | 1981-01-21 |
| FI802002A7 (fi) | 1981-01-01 |
| JPS568363A (en) | 1981-01-28 |
| FR2514352A1 (en, 2012) | 1983-04-15 |
| IL60420A0 (en) | 1980-09-16 |
| ZA803888B (en) | 1982-02-24 |
| FR2460296A1 (fr) | 1981-01-23 |
| DK280380A (da) | 1980-12-30 |
| IT8049093A0 (it) | 1980-06-27 |
| ES492884A0 (es) | 1981-06-01 |
| CA1134370A (en) | 1982-10-26 |
| BE884013A (fr) | 1980-12-29 |
| GB2051811B (en) | 1983-11-23 |
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