DD145537A5 - Verfahren zur herstellung einer 4a,9b-transhexahydro-gamma-carbolin-verbindung - Google Patents

Verfahren zur herstellung einer 4a,9b-transhexahydro-gamma-carbolin-verbindung Download PDF

Info

Publication number: DD145537A5
Authority: DD; German Democratic Republic
Prior art keywords: trans; formula; solvent; methyl; compound
Prior art date: 1977-05-23

Application number

DD78215017A

Other languages

German (de)

English (en)

Inventor

Jun Willard M Welch

Original Assignee

Pfizer

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-05-23

Filing date

1978-05-19

Publication date

1980-12-17

1978-05-19 Application filed by Pfizer filed Critical Pfizer

1980-12-17 Publication of DD145537A5 publication Critical patent/DD145537A5/de

Links

238000000034 method Methods 0.000 title claims description 19
150000001875 compounds Chemical class 0.000 title claims description 18
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 15
-1 chlorofluorocarbonic acid ester Chemical class 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 11
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
229910052731 fluorine Inorganic materials 0.000 claims description 9
239000011737 fluorine Substances 0.000 claims description 8
238000010992 reflux Methods 0.000 claims description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
239000007858 starting material Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 6
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
239000003204 tranquilizing agent Substances 0.000 description 6
230000002936 tranquilizing effect Effects 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
239000002585 base Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
229940035676 analgesics Drugs 0.000 description 2
239000000730 antalgic agent Substances 0.000 description 2
150000007514 bases Chemical class 0.000 description 2
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 description 1
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
YHYKLKNNBYLTQY-UHFFFAOYSA-N 1,1-diphenylhydrazine Chemical compound C=1C=CC=CC=1N(N)C1=CC=CC=C1 YHYKLKNNBYLTQY-UHFFFAOYSA-N 0.000 description 1
DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
VLRGXXKFHVJQOL-UHFFFAOYSA-N 3-chloropentane-2,4-dione Chemical group CC(=O)C(Cl)C(C)=O VLRGXXKFHVJQOL-UHFFFAOYSA-N 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
KMQLIDDEQAJAGJ-UHFFFAOYSA-N 4-oxo-4-phenylbutyric acid Chemical class OC(=O)CCC(=O)C1=CC=CC=C1 KMQLIDDEQAJAGJ-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
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
229910000085 borane Inorganic materials 0.000 description 1
UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000001207 fluorophenyl group Chemical group 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
150000002475 indoles Chemical class 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
229940035363 muscle relaxants Drugs 0.000 description 1
239000003158 myorelaxant agent Substances 0.000 description 1
239000003176 neuroleptic agent Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
229940067157 phenylhydrazine Drugs 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000011084 recovery 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
201000000980 schizophrenia Diseases 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229940125725 tranquilizer Drugs 0.000 description 1
230000005945 translocation Effects 0.000 description 1
239000008096 xylene Substances 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
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- 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
- A61P25/20—Hypnotics; Sedatives
- 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
- A61P25/22—Anxiolytics

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Neurology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Biomedical Technology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Neurosurgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Psychiatry (AREA)
Anesthesiology (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD78215017A 1977-05-23 1978-05-19 Verfahren zur herstellung einer 4a,9b-transhexahydro-gamma-carbolin-verbindung DD145537A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US79939277A	1977-05-23	1977-05-23

Publications (1)

Publication Number	Publication Date
DD145537A5 true DD145537A5 (de)	1980-12-17

Family

ID=25175793

Family Applications (4)

Application Number	Title	Priority Date	Filing Date
DD78215017A DD145537A5 (de)	1977-05-23	1978-05-19	Verfahren zur herstellung einer 4a,9b-transhexahydro-gamma-carbolin-verbindung
DD78205479A DD138321A5 (de)	1977-05-23	1978-05-19	Verfahren zur herstellung von trans-2-substituierten-5-aryl-2,3,4,4a,5,9b-hexahydro-1h-pyrido eckige klammer auf 4,3-b eckige klammer zu-indolinderivaten
DD215016A DD146186A5 (de)	1977-05-23	1978-05-19	Verfahren zur herstellung einer 4a,9b-hexahydro-ypsilon-verbindung
DD78215015A DD145536A5 (de)	1977-05-23	1978-05-19	Verfahren zur herstellung von trans-2-substituierten-5-aryl-2,3,4,4a,5,9b-hexahydro-1h-pyrido(4,3-b)-indolderivaten

Family Applications After (3)

Application Number	Title	Priority Date	Filing Date
DD78205479A DD138321A5 (de)	1977-05-23	1978-05-19	Verfahren zur herstellung von trans-2-substituierten-5-aryl-2,3,4,4a,5,9b-hexahydro-1h-pyrido eckige klammer auf 4,3-b eckige klammer zu-indolinderivaten
DD215016A DD146186A5 (de)	1977-05-23	1978-05-19	Verfahren zur herstellung einer 4a,9b-hexahydro-ypsilon-verbindung
DD78215015A DD145536A5 (de)	1977-05-23	1978-05-19	Verfahren zur herstellung von trans-2-substituierten-5-aryl-2,3,4,4a,5,9b-hexahydro-1h-pyrido(4,3-b)-indolderivaten

Country Status (31)

Country	Link
JP (1)	JPS53144600A (fr)
AR (2)	AR217688A1 (fr)
AT (1)	AT368995B (fr)
AU (1)	AU499618B1 (fr)
BE (1)	BE867249A (fr)
CA (1)	CA1094071A (fr)
CH (1)	CH634321A5 (fr)
CS (1)	CS207612B2 (fr)
DD (4)	DD145537A5 (fr)
DE (1)	DE2822465C2 (fr)
DK (1)	DK226678A (fr)
EG (1)	EG13590A (fr)
FI (1)	FI63402C (fr)
FR (1)	FR2392023A1 (fr)
GB (1)	GB1586655A (fr)
GR (1)	GR69985B (fr)
HU (3)	HU185009B (fr)
IE (1)	IE46975B1 (fr)
IL (1)	IL54755A (fr)
IT (1)	IT1096307B (fr)
LU (1)	LU79684A1 (fr)
NL (1)	NL7804210A (fr)
NO (2)	NO150204C (fr)
NZ (1)	NZ187333A (fr)
PH (1)	PH13756A (fr)
PL (5)	PL114547B1 (fr)
PT (1)	PT68058B (fr)
SE (2)	SE441448B (fr)
SU (4)	SU873883A3 (fr)
YU (4)	YU91478A (fr)
ZA (1)	ZA782918B (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4224329A (en) *	1979-01-23	1980-09-23	Pfizer Inc.	2-Substituted-trans-5-aryl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indoles
US4451655A (en) *	1982-05-17	1984-05-29	Pfizer Inc.	Process for preparing carboline derivatives and compounds used in their preparation
RU2106864C1 (ru) *	1995-10-23	1998-03-20	Николай Серафимович Зефиров	Средство для лечения болезни альцгеймера
SE9604786D0 (sv) *	1996-12-20	1996-12-20	Astra Pharma Inc	New compounds
US6974825B1 (en)	1996-12-20	2005-12-13	Astrazeneca Canada Inc.	Compounds with analgesic effect
SE9904675D0 (sv)	1999-12-20	1999-12-20	Astra Pharma Inc	Novel compounds
SE0101771D0 (sv)	2001-05-18	2001-05-18	Astrazeneca Ab	Novel compounds
SE0101773D0 (sv)	2001-05-18	2001-05-18	Astrazeneca Ab	Novel compounds
SE0101770D0 (sv)	2001-05-18	2001-05-18	Astrazeneca Ab	Novel compounds
SE0101769D0 (sv)	2001-05-18	2001-05-18	Astrazeneca Ab	Novel compounds

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AR205452A1 (es) *	1973-12-06	1976-05-07	Endo Lab	Metodo para preparar nuevos trans-2, 3, 4, 4a, 5, 9b-hexahidro-5-fenil-1h-pirido(4,3-b) indoles
JPS50126699A (fr) *	1974-03-20	1975-10-04
US4001263A (en) *	1974-04-01	1977-01-04	Pfizer Inc.	5-Aryl-1,2,3,4-tetrahydro-γ-carbolines

1978
- 1978-03-30 SE SE7803625A patent/SE441448B/sv unknown
- 1978-04-17 PH PH21013A patent/PH13756A/en unknown
- 1978-04-18 YU YU00914/78A patent/YU91478A/xx unknown
- 1978-04-20 NL NL7804210A patent/NL7804210A/xx not_active Application Discontinuation
- 1978-04-24 AU AU35377/78A patent/AU499618B1/en not_active Expired
- 1978-04-25 EG EG276/78A patent/EG13590A/xx active
- 1978-04-28 AR AR271956A patent/AR217688A1/es active
- 1978-05-18 SU SU782615898A patent/SU873883A3/ru active
- 1978-05-18 CS CS783239A patent/CS207612B2/cs unknown
- 1978-05-18 HU HU78PI626A patent/HU185009B/hu unknown
- 1978-05-18 HU HU822638A patent/HU188802B/hu unknown
- 1978-05-18 PL PL1978206903A patent/PL114547B1/pl unknown
- 1978-05-18 PL PL1978215921A patent/PL117107B1/pl unknown
- 1978-05-18 PL PL1978215922A patent/PL114541B1/pl unknown
- 1978-05-18 HU HU822639A patent/HU187782B/hu unknown
- 1978-05-18 PL PL1978215923A patent/PL116944B1/pl unknown
- 1978-05-18 GB GB20350/78A patent/GB1586655A/en not_active Expired
- 1978-05-19 PT PT68058A patent/PT68058B/pt unknown
- 1978-05-19 BE BE187842A patent/BE867249A/fr not_active IP Right Cessation
- 1978-05-19 CA CA303,710A patent/CA1094071A/fr not_active Expired
- 1978-05-19 DD DD78215017A patent/DD145537A5/de unknown
- 1978-05-19 DD DD78205479A patent/DD138321A5/xx unknown
- 1978-05-19 DD DD215016A patent/DD146186A5/de unknown
- 1978-05-19 DD DD78215015A patent/DD145536A5/de unknown
- 1978-05-20 GR GR56281A patent/GR69985B/el unknown
- 1978-05-22 DK DK226678A patent/DK226678A/da not_active Application Discontinuation
- 1978-05-22 IE IE1013/78A patent/IE46975B1/en unknown
- 1978-05-22 FR FR7815029A patent/FR2392023A1/fr active Granted
- 1978-05-22 FI FI781612A patent/FI63402C/fi not_active IP Right Cessation
- 1978-05-22 NZ NZ187333A patent/NZ187333A/en unknown
- 1978-05-22 ZA ZA00782918A patent/ZA782918B/xx unknown
- 1978-05-22 NO NO781770A patent/NO150204C/no unknown
- 1978-05-22 JP JP6087278A patent/JPS53144600A/ja active Granted
- 1978-05-22 LU LU79684A patent/LU79684A1/fr unknown
- 1978-05-22 CH CH552678A patent/CH634321A5/fr not_active IP Right Cessation
- 1978-05-22 IL IL54755A patent/IL54755A/xx unknown
- 1978-05-22 IT IT23673/78A patent/IT1096307B/it active
- 1978-05-22 AT AT0369678A patent/AT368995B/de not_active IP Right Cessation
- 1978-05-23 DE DE2822465A patent/DE2822465C2/de not_active Expired
1979
- 1979-04-16 AR AR276191A patent/AR221721A1/es active
- 1979-04-24 SU SU792753359A patent/SU843749A3/ru active
- 1979-04-26 SU SU792759902A patent/SU818484A3/ru active
- 1979-05-18 SU SU792763595A patent/SU841589A3/ru active
- 1979-05-18 PL PL20690379A patent/PL206903A1/xx unknown
1982
- 1982-10-01 YU YU02218/82A patent/YU221882A/xx unknown
- 1982-10-01 YU YU2217/82A patent/YU40796B/xx unknown
- 1982-10-01 YU YU02216/82A patent/YU221682A/xx unknown
1983
- 1983-05-20 NO NO831790A patent/NO151862C/no unknown
- 1983-10-27 SE SE8305917A patent/SE448459B/sv not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK226678A (da)	1978-11-24
ZA782918B (en)	1979-06-27
PH13756A (en)	1980-09-17
NZ187333A (en)	1984-05-31
FR2392023B1 (fr)	1980-11-07
NL7804210A (nl)	1978-11-27
PL114547B1 (en)	1981-02-28
NO151862B (no)	1985-03-11
NO831790L (no)	1978-11-24
IE781013L (en)	1978-11-23
SU818484A3 (ru)	1981-03-30
HU185009B (en)	1984-11-28
NO150204C (no)	1984-09-05
SU873883A3 (ru)	1981-10-15
SU841589A3 (ru)	1981-06-23
FI63402C (fi)	1983-06-10
IL54755A (en)	1981-02-27
IT7823673A0 (it)	1978-05-22
PL116944B1 (en)	1981-07-31
NO151862C (no)	1985-06-19
LU79684A1 (fr)	1979-12-06
GB1586655A (en)	1981-03-25
IL54755A0 (en)	1978-07-31
FR2392023A1 (fr)	1978-12-22
YU221782A (en)	1983-01-21
YU221882A (en)	1983-01-21
FI63402B (fi)	1983-02-28
GR69985B (fr)	1982-07-22
PL114541B1 (en)	1981-02-28
SU843749A3 (ru)	1981-06-30
CA1094071A (fr)	1981-01-20
FI781612A7 (fi)	1978-11-24
PT68058B (en)	1979-10-24
CS207612B2 (en)	1981-08-31
SE441448B (sv)	1985-10-07
NO150204B (no)	1984-05-28
DD146186A5 (de)	1981-01-28
JPS53144600A (en)	1978-12-15
AR221721A1 (es)	1981-03-13
PT68058A (en)	1978-06-01
AU499618B1 (en)	1979-04-26
YU40796B (en)	1986-06-30
ATA369678A (de)	1982-04-15
DE2822465C2 (de)	1986-08-28
EG13590A (en)	1982-03-31
JPS5711912B2 (fr)	1982-03-08
AT368995B (de)	1982-11-25
AR217688A1 (es)	1980-04-15
CH634321A5 (en)	1983-01-31
HU187782B (en)	1986-02-28
DD145536A5 (de)	1980-12-17
SE8305917D0 (sv)	1983-10-27
DE2822465A1 (de)	1978-11-30
BE867249A (fr)	1978-11-20
SE8305917L (sv)	1983-10-27
PL206903A1 (pl)	1979-10-22
SE7803625L (sv)	1978-11-24
IT1096307B (it)	1985-08-26
IE46975B1 (en)	1983-11-16
YU221682A (en)	1983-01-21
SE448459B (sv)	1987-02-23
NO781770L (no)	1978-11-24
PL117107B1 (en)	1981-07-31
YU91478A (en)	1983-01-21
DD138321A5 (de)	1979-10-24
HU188802B (en)	1986-05-28

Publication	Publication Date	Title
DE69634639T2 (de)	2006-03-02	Verfahren zur herstellung optische aktive verbindungen
EP0173199B1 (fr)	1994-07-13	Dérivés de l'acide cis, endo-aza-2 bicycloalcane carboxylique-3, procédés pour leur préparation et les produits intermédiaires lors de leur préparation
DD156369A5 (de)	1982-08-18	Herstellung von rechtsdrehenden 5-aryl-2,3,4,4a,5,9b-hexahydro-1h-pyrido[4,3b]-indolen
EP0385210B1 (fr)	1995-02-15	Amidification de pyridines
DE2822465C2 (de)	1986-08-28	2-substituierte trans-5-Phenyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indolderivate und diese enthaltende Arzneimittel
DE2016721A1 (fr)	1970-10-29
DE69520071T2 (de)	2001-09-13	Substituierte tetracyclische oxazepine- und thiazepinederivate mit 5-ht2 rezeptoraffinität
DE2840770C2 (fr)	1987-07-16
DD292913A5 (de)	1991-08-14	Verfahren zur herstellung neuer benzothiopyranylamine
EP0090769B1 (fr)	1986-08-20	Procédé pour la préparation de la 1,2,5,6-tétrahydro-4H-pyrrolo(3,2,1-ij)-quinoléin-4-one et 5-halo-1,2,3-(1,2-dihydropyrrolo)-4-quinolones intermédiaires
DE19853558A1 (de)	2000-05-31	Verfahren zur Herstellung von 2,3-Dihydroindolen (Indolinen), neuartige 2,3-Dihydroindole sowie deren Verwendung
AT368996B (de)	1982-11-25	Verfahren zur herstellung von neuen hexahydro -gamma-carbolinverbindungen
DE3026602A1 (de)	1981-02-05	14-oxo-15-halogen-e-homoeburnanderivate, verfahren zur herstellung derselben und von 14-oxo-15-hydroxyimino-e-homoeburnanderivaten und die ersteren enthaltende arzneimittel
DD206986A5 (de)	1984-02-15	Verfahren zur herstellung von pharmakologisch wirksamen 4-/2-hydroxy-4-(subst.)phenyl/-naphthalin-2(1h)-onen und -2-olen
DE102004004965B4 (de)	2006-01-05	Verfahren zur Herstellung eines 2-(Ethoxymethyl)-tropanderivates
DE2534601A1 (de)	1977-02-17	Verfahren zur herstellung von camptothecin-aehnlichen verbindungen
DE2354327B2 (de)	1977-12-08	2-amino-1,2,3,4-tetrahydronaphthalin- derivate, verfahren zu deren herstellung und verfahren zur herstellung von 6,7- benzomorphanen ausgehend von jenen
DE3707530A1 (de)	1987-09-17	Neue substituierte dihalogenpyridine und verfahren zu ihrer herstellung sowie ihre weitere umsetzung zu pyridindicarbonsaeurediestern
DE2017470A1 (fr)	1970-10-29
CH634559A5 (de)	1983-02-15	Verfahren zur herstellung von 3-halogen-3-kohlenwasserstoffthio-oxindolen und verfahren zur herstellung von isatinen.
DE2628469B2 (de)	1980-06-04	Verfahren zur Herstellung von γ -Aminoalkoholen
DE10304141A1 (de)	2004-08-26	Verfahren zur Herstellung von Chinazolin-Alkaloiden
DE2931295A1 (de)	1980-02-28	Verfahren zur herstellung von optisch rechtsdrehenden 1-aethyl-1-(2'-alkoxycarbonylaethyl)-1,2,3,4,6,7,12,12b- octahydroindolo eckige klammer auf 2,3-a eckige klammer zu chinolizinen
AT335458B (de)	1977-03-10	Verfahren zur herstellung von neuen 2-substituierten 1,2,3,4,6,7,12,12a-octahydropyrazino-(2',1':6,1)-pyrido-(3,4-b)-indolen und ihren salzen
DE2655004B2 (de)	1979-09-27	Verfahren zur Herstellung von bicyclischen Laktonen