CY1399A - 4,5,5a-6-tetrahydrodibenz(cd,f) indoles - Google Patents
4,5,5a-6-tetrahydrodibenz(cd,f) indoles Download PDFInfo
- Publication number
- CY1399A CY1399A CY139981A CY139981A CY1399A CY 1399 A CY1399 A CY 1399A CY 139981 A CY139981 A CY 139981A CY 139981 A CY139981 A CY 139981A CY 1399 A CY1399 A CY 1399A
- Authority
- CY
- Cyprus
- Prior art keywords
- compound
- ethyl
- tetrahydro
- dibenz
- propyl
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- 150000002475 indoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 75
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 56
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 28
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 28
- -1 isobutyryloxy Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 150000003839 salts Chemical group 0.000 claims description 9
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 8
- 125000001033 ether group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 239000012458 free base Substances 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
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- 125000004423 acyloxy group Chemical group 0.000 claims 1
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- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 201000008275 breast carcinoma Diseases 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000012505 colouration Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- MHUWZNTUIIFHAS-CLFAGFIQSA-N dioleoyl phosphatidic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCC MHUWZNTUIIFHAS-CLFAGFIQSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003136 dopamine receptor stimulating agent Substances 0.000 description 1
- 229940005501 dopaminergic agent Drugs 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 208000031424 hyperprolactinemia Diseases 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 201000001881 impotence Diseases 0.000 description 1
- 208000000509 infertility Diseases 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 231100000535 infertility Toxicity 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000006651 lactation Effects 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 229960004502 levodopa Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000033001 locomotion Effects 0.000 description 1
- UGVPKMAWLOMPRS-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].CC[CH2-] UGVPKMAWLOMPRS-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000002175 menstrual effect Effects 0.000 description 1
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical class [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- NGHSAAXKBIWRBD-UHFFFAOYSA-N n-(3-bromo-3,4-dimethoxy-2h-phenanthren-9-yl)-n-ethylbutanamide Chemical compound C1=CC=C2C(N(CC)C(=O)CCC)=CC3=CCC(Br)(OC)C(OC)=C3C2=C1 NGHSAAXKBIWRBD-UHFFFAOYSA-N 0.000 description 1
- MJFVSNHXRYJOLC-UHFFFAOYSA-N n-amino-n-benzylhydroxylamine Chemical compound NN(O)CC1=CC=CC=C1 MJFVSNHXRYJOLC-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- DIVDFFZHCJEHGG-UHFFFAOYSA-N oxidopamine Chemical compound NCCC1=CC(O)=C(O)C=C1O DIVDFFZHCJEHGG-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 210000003523 substantia nigra Anatomy 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229960005333 tetrabenazine Drugs 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000028838 turning behavior Effects 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH497280 | 1980-06-27 | ||
| GB8037586 | 1980-11-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CY1399A true CY1399A (en) | 1987-12-18 |
Family
ID=25696642
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CY139981A CY1399A (en) | 1980-06-27 | 1981-06-24 | 4,5,5a-6-tetrahydrodibenz(cd,f) indoles |
Country Status (22)
| Country | Link |
|---|---|
| AT (1) | AT380875B (enExample) |
| AU (1) | AU546599B2 (enExample) |
| CA (1) | CA1155447A (enExample) |
| CY (1) | CY1399A (enExample) |
| DE (1) | DE3124086A1 (enExample) |
| DK (1) | DK285481A (enExample) |
| ES (3) | ES8300701A1 (enExample) |
| FI (1) | FI75153C (enExample) |
| FR (2) | FR2485530A1 (enExample) |
| GB (1) | GB2136418B (enExample) |
| IE (1) | IE51341B1 (enExample) |
| IL (1) | IL63174A (enExample) |
| IT (1) | IT8148776A0 (enExample) |
| KE (1) | KE3749A (enExample) |
| NL (1) | NL8103041A (enExample) |
| NZ (1) | NZ197529A (enExample) |
| PH (1) | PH22773A (enExample) |
| PT (1) | PT73258B (enExample) |
| SE (1) | SE449222B (enExample) |
| SG (1) | SG62087G (enExample) |
| WO (1) | WO1982000143A1 (enExample) |
| YU (1) | YU159481A (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH647507A5 (de) * | 1982-04-13 | 1985-01-31 | Sandoz Ag | Heterozyklische verbindungen, verfahren zu deren herstellung und pharmazeutische zusammensetzungen, welche diese verbindungen enthalten. |
| AT381090B (de) * | 1983-04-12 | 1986-08-25 | Sandoz Ag | Herstellung von neuen (4r*,5as*)2,4,5-trialkylch8204132231/8 |
| US4795759A (en) * | 1985-07-27 | 1989-01-03 | Sandoz Ltd. | Use of dibenz(CD,F)indoles |
| US5220536A (en) * | 1989-09-01 | 1993-06-15 | Quantronix, Inc. | Measuring method and apparatus |
| US5422861A (en) * | 1989-09-01 | 1995-06-06 | Quantronix, Inc. | Measuring method and apparatus |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE877169A (fr) * | 1978-06-23 | 1979-12-21 | Sandoz Sa | Nouveaux derives du phenantrene, leur preparation et leur application comme medicaments |
| DK249379A (da) * | 1978-06-23 | 1980-01-22 | Sandoz Ag | Fremgangsmaade til fremstilling af phenanthrenderivater |
-
1981
- 1981-06-18 FI FI811922A patent/FI75153C/fi not_active IP Right Cessation
- 1981-06-19 DE DE19813124086 patent/DE3124086A1/de not_active Withdrawn
- 1981-06-22 FR FR8112367A patent/FR2485530A1/fr active Granted
- 1981-06-22 AU AU72028/81A patent/AU546599B2/en not_active Ceased
- 1981-06-24 WO PCT/CH1981/000069 patent/WO1982000143A1/de not_active Ceased
- 1981-06-24 CY CY139981A patent/CY1399A/en unknown
- 1981-06-24 NL NL8103041A patent/NL8103041A/nl not_active Application Discontinuation
- 1981-06-25 PT PT73258A patent/PT73258B/pt unknown
- 1981-06-25 NZ NZ197529A patent/NZ197529A/en unknown
- 1981-06-25 IL IL63174A patent/IL63174A/xx unknown
- 1981-06-25 SE SE8103983A patent/SE449222B/sv not_active IP Right Cessation
- 1981-06-25 YU YU01594/81A patent/YU159481A/xx unknown
- 1981-06-25 IE IE1421/81A patent/IE51341B1/en unknown
- 1981-06-25 CA CA000380614A patent/CA1155447A/en not_active Expired
- 1981-06-26 AT AT0284481A patent/AT380875B/de not_active IP Right Cessation
- 1981-06-26 DK DK285481A patent/DK285481A/da not_active Application Discontinuation
- 1981-06-26 ES ES503432A patent/ES8300701A1/es not_active Expired
- 1981-06-26 IT IT8148776A patent/IT8148776A0/it unknown
- 1981-06-26 PH PH25823A patent/PH22773A/en unknown
-
1982
- 1982-09-02 FR FR8215401A patent/FR2510996A1/fr not_active Withdrawn
- 1982-09-08 ES ES515568A patent/ES515568A0/es active Granted
- 1982-09-08 ES ES515567A patent/ES8400088A1/es not_active Expired
-
1983
- 1983-09-27 GB GB08325760A patent/GB2136418B/en not_active Expired
-
1987
- 1987-07-31 SG SG620/87A patent/SG62087G/en unknown
- 1987-08-14 KE KE3749A patent/KE3749A/xx unknown
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