CH602734A5 - Vincanol derivs - Google Patents

Vincanol derivs

Info

Publication number: CH602734A5
Authority: CH; Switzerland
Prior art keywords: formula; compounds; vincanol; derivs; aminoalkyl
Prior art date: 1974-09-06

Application number

CH1215374A

Other languages

German (de)

English (en)

Inventor

Paul Pfaeffli

Original Assignee

Sandoz Ag

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.)

1974-09-06

Filing date

1974-09-06

Publication date

1978-07-31

1974-09-06 Application filed by Sandoz Ag filed Critical Sandoz Ag

1974-09-06 Priority to CH1215374A priority Critical patent/CH602734A5/de

1975-08-27 Priority to DE19752538095 priority patent/DE2538095A1/de

1975-08-28 Priority to FI752423A priority patent/FI752423A7/fi

1975-08-28 Priority to DK388475A priority patent/DK388475A/da

1975-08-29 Priority to NO752972A priority patent/NO752972L/no

1975-08-29 Priority to SE7509657A priority patent/SE7509657L/xx

1975-09-02 Priority to US05/609,357 priority patent/US4045443A/en

1975-09-02 Priority to NL7510315A priority patent/NL7510315A/xx

1975-09-02 Priority to FR7526884A priority patent/FR2342065A1/fr

1975-09-03 Priority to GB36242/75A priority patent/GB1518987A/en

1975-09-04 Priority to BE159751A priority patent/BE833080A/fr

1975-09-04 Priority to DD188188A priority patent/DD121943A5/xx

1975-09-04 Priority to IL48054A priority patent/IL48054A/xx

1975-09-04 Priority to ES440723A priority patent/ES440723A1/es

1975-09-04 Priority to AU84567/75A priority patent/AU8456775A/en

1975-09-05 Priority to AT685475A priority patent/ATA685475A/de

1975-09-05 Priority to JP50107161A priority patent/JPS5154600A/ja

1975-09-05 Priority to ZA755697A priority patent/ZA755697B/xx

1977-03-01 Priority to ES456416A priority patent/ES456416A1/es

1977-04-18 Priority to US05/788,510 priority patent/US4123535A/en

1978-07-31 Publication of CH602734A5 publication Critical patent/CH602734A5/de

Links

229950002496 vincanol Drugs 0.000 title abstract description 5
HONLKDDLTAZVQV-UHFFFAOYSA-N eburnamine Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)CC(O)N5C2=C1 HONLKDDLTAZVQV-UHFFFAOYSA-N 0.000 title abstract description 4
HONLKDDLTAZVQV-UHOSZYNNSA-N vincanol Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@H](O)N5C2=C1 HONLKDDLTAZVQV-UHOSZYNNSA-N 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims description 20
229910000039 hydrogen halide Inorganic materials 0.000 claims description 7
239000012433 hydrogen halide Substances 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
VKTOXAGUZWAECL-OALUTQOASA-N eburnamenine Natural products C1=CC=C2C(CCN3CCC4)=C5[C@H]3[C@]4(CC)C=CN5C2=C1 VKTOXAGUZWAECL-OALUTQOASA-N 0.000 claims description 6
VKTOXAGUZWAECL-UHFFFAOYSA-N trans-eburnamenine Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)C=CN5C2=C1 VKTOXAGUZWAECL-UHFFFAOYSA-N 0.000 claims description 6
125000004103 aminoalkyl group Chemical group 0.000 claims description 5
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
238000000034 method Methods 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims 1
230000002490 cerebral effect Effects 0.000 abstract description 2
208000009999 tuberous sclerosis Diseases 0.000 abstract description 2
206010047095 Vascular pain Diseases 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
238000003756 stirring Methods 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
229910000042 hydrogen bromide Inorganic materials 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000002904 solvent Substances 0.000 description 2
206010001497 Agitation Diseases 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
206010019196 Head injury Diseases 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
206010062519 Poor quality sleep Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
208000003443 Unconsciousness Diseases 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
230000037396 body weight Effects 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000003970 cerebral vascular damage Effects 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000002002 slurry Substances 0.000 description 1
SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
230000017105 transposition Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D461/00—Heterocyclic compounds containing indolo [3,2,1-d,e] pyrido [3,2,1,j] [1,5]-naphthyridine ring systems, e.g. vincamine

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH1215374A 1974-09-06 1974-09-06 Vincanol derivs CH602734A5 (en)

Priority Applications (20)

Application Number	Priority Date	Filing Date	Title
CH1215374A CH602734A5 (en)	1974-09-06	1974-09-06	Vincanol derivs
DE19752538095 DE2538095A1 (de)	1974-09-06	1975-08-27	Neue organische verbindungen, ihre herstellung und verwendung
FI752423A FI752423A7 (fr)	1974-09-06	1975-08-28
DK388475A DK388475A (da)	1974-09-06	1975-08-28	Fremgangsmade til fremstilling af polycycliske nitrogenholdige forbindelser
NO752972A NO752972L (fr)	1974-09-06	1975-08-29
SE7509657A SE7509657L (sv)	1974-09-06	1975-08-29	Forfarande for framstellning och anvendning av nya organiska foreningar
US05/609,357 US4045443A (en)	1974-09-06	1975-09-02	Organic compounds
NL7510315A NL7510315A (nl)	1974-09-06	1975-09-02	Werkwijze ter bereiding van nieuwe organische verbindingen.
FR7526884A FR2342065A1 (fr)	1974-09-06	1975-09-02	Nouveaux composes heterocycliques, leur preparation et leur application comme medicaments
GB36242/75A GB1518987A (en)	1974-09-06	1975-09-03	Heterocyclic compounds
BE159751A BE833080A (fr)	1974-09-06	1975-09-04	Nouveaux composes heterocycliques, leur preparation et leur application comme medicaments
DD188188A DD121943A5 (fr)	1974-09-06	1975-09-04
IL48054A IL48054A (en)	1974-09-06	1975-09-04	14-deoxy-14-substituted vincanol derivatives their production and pharmaceutical compositions containing them
ES440723A ES440723A1 (es)	1974-09-06	1975-09-04	Procedimiento para la produccion de nuevos compuestos orga- nicos.
AU84567/75A AU8456775A (en)	1974-09-06	1975-09-04	Vinca alkaloids
AT685475A ATA685475A (de)	1974-09-06	1975-09-05	Verfahren zur herstellung neuer vincanol- und epivincanolderivate
JP50107161A JPS5154600A (fr)	1974-09-06	1975-09-05
ZA755697A ZA755697B (en)	1974-09-06	1975-09-05	Improvements in or relating to organic compounds
ES456416A ES456416A1 (es)	1974-09-06	1977-03-01	Procedimiento para la obtencion de derivados de 14-dioxi- vincanol.
US05/788,510 US4123535A (en)	1974-09-06	1977-04-18	Psychostimulating 14-amino-14,15-dihydroeburnamenines

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1215374A CH602734A5 (en)	1974-09-06	1974-09-06	Vincanol derivs

Publications (1)

Publication Number	Publication Date
CH602734A5 true CH602734A5 (en)	1978-07-31

Family

ID=4380368

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1215374A CH602734A5 (en)	1974-09-06	1974-09-06	Vincanol derivs

Country Status (4)

Country	Link
AT (1)	ATA685475A (fr)
BE (1)	BE833080A (fr)
CH (1)	CH602734A5 (fr)
ZA (1)	ZA755697B (fr)

1974
- 1974-09-06 CH CH1215374A patent/CH602734A5/de not_active IP Right Cessation
1975
- 1975-09-04 BE BE159751A patent/BE833080A/fr unknown
- 1975-09-05 AT AT685475A patent/ATA685475A/de not_active Application Discontinuation
- 1975-09-05 ZA ZA755697A patent/ZA755697B/xx unknown

Also Published As

Publication number	Publication date
ZA755697B (en)	1977-04-27
BE833080A (fr)	1976-03-04
ATA685475A (de)	1979-02-15

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Legal Events

Date	Code	Title	Description
1981-05-29	PL	Patent ceased
2024-10-31	PL	Patent ceased