DD295378A5 - Stereoselektives hydrierungsverfahren - Google Patents

Stereoselektives hydrierungsverfahren Download PDF

Info

Publication number: DD295378A5
Authority: DD; German Democratic Republic
Prior art keywords: lysergol; hydrogenation; dihydrolysergol; solvent; catalyst
Prior art date: 1989-06-27

Application number

DD90342087A

Other languages

German (de)

English (en)

Inventor

Istvan Polgar

Jozsef Foeldesi

Janos Kiss

Piroska Major

Karoly Molnar

Andras Sugar

Tamas Szen

Katalin Balogh

Original Assignee

��@��@��@��@�K@�Kk��

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.)

1989-06-27

Filing date

1990-06-26

Publication date

1991-10-31

1990-06-26 Application filed by ��@��@��@��@�K@�Kk�� filed Critical ��@��@��@��@�K@�Kk��

1991-10-31 Publication of DD295378A5 publication Critical patent/DD295378A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 21
238000011924 stereoselective hydrogenation Methods 0.000 title abstract description 4
239000003054 catalyst Substances 0.000 claims abstract description 31
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 27
BIXJFIJYBLJTMK-MEBBXXQBSA-N lysergol Chemical compound C1=CC(C2=C[C@@H](CO)CN([C@@H]2C2)C)=C3C2=CNC3=C1 BIXJFIJYBLJTMK-MEBBXXQBSA-N 0.000 claims abstract description 19
BIXJFIJYBLJTMK-UHFFFAOYSA-N Lysergol Natural products C1=CC(C2=CC(CO)CN(C2C2)C)=C3C2=CNC3=C1 BIXJFIJYBLJTMK-UHFFFAOYSA-N 0.000 claims abstract description 18
239000002904 solvent Substances 0.000 claims abstract description 15
UFKTZIXVYHGAES-WDBKCZKBSA-N [(6ar,9r,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]methanol Chemical compound C1=CC([C@H]2C[C@@H](CO)CN([C@@H]2C2)C)=C3C2=CNC3=C1 UFKTZIXVYHGAES-WDBKCZKBSA-N 0.000 claims abstract description 14
UFKTZIXVYHGAES-UHFFFAOYSA-N trans-dihydrolysergol Natural products C1=CC(C2CC(CO)CN(C2C2)C)=C3C2=CNC3=C1 UFKTZIXVYHGAES-UHFFFAOYSA-N 0.000 claims abstract description 14
229910052763 palladium Inorganic materials 0.000 claims abstract description 13
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
239000011541 reaction mixture Substances 0.000 claims abstract description 7
238000002360 preparation method Methods 0.000 claims abstract description 4
238000005984 hydrogenation reaction Methods 0.000 claims description 20
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 5
238000009835 boiling Methods 0.000 claims description 2
230000000707 stereoselective effect Effects 0.000 claims description 2
UFKTZIXVYHGAES-SKNXHYNKSA-N [(6ar,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]methanol Chemical compound C1=CC([C@H]2CC(CO)CN([C@@H]2C2)C)=C3C2=CNC3=C1 UFKTZIXVYHGAES-SKNXHYNKSA-N 0.000 claims 1
239000003610 charcoal Substances 0.000 abstract description 2
238000004519 manufacturing process Methods 0.000 abstract description 2
238000006243 chemical reaction Methods 0.000 description 7
239000000047 product Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000007086 side reaction Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
QOTUIZVGUVLMNQ-GJLSPIEVSA-N (6aR)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide (6aR)-N-[(1S,2S,4R,7S)-2-hydroxy-5,8-dioxo-4,7-di(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide (6aR)-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide Chemical compound CC(C)[C@@H]1N2C(=O)[C@](NC(=O)C3CN(C)[C@@H]4Cc5c[nH]c6cccc(C4=C3)c56)(O[C@@]2(O)[C@@H]2CCCN2C1=O)C(C)C.CC(C)C[C@@H]1N2C(=O)[C@](NC(=O)C3CN(C)[C@@H]4Cc5c[nH]c6cccc(C4=C3)c56)(O[C@@]2(O)[C@@H]2CCCN2C1=O)C(C)C.CC(C)[C@@]1(NC(=O)C2CN(C)[C@@H]3Cc4c[nH]c5cccc(C3=C2)c45)O[C@@]2(O)[C@@H]3CCCN3C(=O)[C@H](Cc3ccccc3)N2C1=O QOTUIZVGUVLMNQ-GJLSPIEVSA-N 0.000 description 1
GOYFTNUGZJYXDW-QPUOJXLNSA-N (6aR,9R)-7,9-dimethyl-4,5,5a,6,6a,8-hexahydroindolo[4,3-fg]quinoline-9-carboxylic acid Chemical compound C1NC2=CC=CC3=C2C1C[C@@H]1C3=C[C@@](C)(C(O)=O)CN1C GOYFTNUGZJYXDW-QPUOJXLNSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000000824 cytostatic agent Substances 0.000 description 1
230000001085 cytostatic effect Effects 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
RHGUXDUPXYFCTE-ZWNOBZJWSA-N ergoline Chemical class C1=CC([C@@H]2[C@H](NCCC2)C2)=C3C2=CNC3=C1 RHGUXDUPXYFCTE-ZWNOBZJWSA-N 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
-1 lithium aluminum hydride Chemical compound 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical class C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000009901 transfer hydrogenation reaction Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/02—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hydrocarbon or substituted hydrocarbon radicals, attached in position 8

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD90342087A 1989-06-27 1990-06-26 Stereoselektives hydrierungsverfahren DD295378A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU893225A HU203549B (en)	1989-06-27	1989-06-27	New stereoselektive hydrogenating process for producing dihydro-lisergol

Publications (1)

Publication Number	Publication Date
DD295378A5 true DD295378A5 (de)	1991-10-31

Family

ID=10963194

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90342087A DD295378A5 (de)	1989-06-27	1990-06-26	Stereoselektives hydrierungsverfahren

Country Status (14)

Country	Link
US (1)	US5097031A (fr)
JP (1)	JPH03128374A (fr)
CA (1)	CA2019407C (fr)
CH (1)	CH680445A5 (fr)
CZ (1)	CZ281957B6 (fr)
DD (1)	DD295378A5 (fr)
DE (1)	DE4020475A1 (fr)
FI (1)	FI92586C (fr)
FR (1)	FR2648815B1 (fr)
HU (1)	HU203549B (fr)
IT (1)	IT1249001B (fr)
NL (1)	NL9001459A (fr)
RU (1)	RU1779253C (fr)
YU (1)	YU124790A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN101481405A (zh)	2001-06-08	2009-07-15	研究及应用科学协会股份有限公司	生长激素释放抑制因子-多巴胺嵌合类似物

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE107647T1 (de) *	1984-04-09	1994-07-15	Schering Ag	2-substituierte ergolin-derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel.
CH658058A5 (en) *	1984-06-21	1986-10-15	Linnea Sa	Process for preparing lumilysergol derivatives

1989
- 1989-06-27 HU HU893225A patent/HU203549B/hu not_active IP Right Cessation
1990
- 1990-06-20 CA CA002019407A patent/CA2019407C/fr not_active Expired - Fee Related
- 1990-06-21 FR FR909007757A patent/FR2648815B1/fr not_active Expired - Lifetime
- 1990-06-22 US US07/542,168 patent/US5097031A/en not_active Expired - Lifetime
- 1990-06-26 CH CH2131/90A patent/CH680445A5/de not_active IP Right Cessation
- 1990-06-26 FI FI903196A patent/FI92586C/fi not_active IP Right Cessation
- 1990-06-26 NL NL9001459A patent/NL9001459A/nl not_active Application Discontinuation
- 1990-06-26 JP JP2165835A patent/JPH03128374A/ja active Pending
- 1990-06-26 IT IT02076990A patent/IT1249001B/it active IP Right Grant
- 1990-06-26 DD DD90342087A patent/DD295378A5/de not_active IP Right Cessation
- 1990-06-26 YU YU01247/90A patent/YU124790A/xx unknown
- 1990-06-27 DE DE4020475A patent/DE4020475A1/de not_active Withdrawn
- 1990-06-27 RU SU904830539A patent/RU1779253C/ru active
- 1990-06-27 CZ CS903211A patent/CZ281957B6/cs not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPH03128374A (ja)	1991-05-31
IT1249001B (it)	1995-02-11
FI92586C (fi)	1994-12-12
CZ281957B6 (cs)	1997-04-16
CA2019407A1 (fr)	1990-12-27
DE4020475A1 (de)	1991-02-07
RU1779253C (ru)	1992-11-30
US5097031A (en)	1992-03-17
CH680445A5 (fr)	1992-08-31
FR2648815A1 (fr)	1990-12-28
NL9001459A (nl)	1991-01-16
IT9020769A0 (it)	1990-06-26
IT9020769A1 (it)	1991-12-26
YU124790A (en)	1991-10-31
FI903196A0 (fi)	1990-06-26
HU203549B (en)	1991-08-28
CA2019407C (fr)	1997-09-30
CZ321190A3 (en)	1997-01-15
FR2648815B1 (fr)	1992-08-14
FI92586B (fi)	1994-08-31

Legal Events

Date	Code	Title	Description
2001-01-18	ENJ	Ceased due to non-payment of renewal fee

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DE3881024T2 (de)	1993-08-19	Verfahren zur herstellung von tetracyclin.
EP0032684B1 (fr)	1985-11-21	Procédé de préparation de 6-méthylergolines substituées en position 8 alpha
DE3443385C2 (fr)	1987-05-27
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DD263288A5 (de)	1988-12-28	Verfahren zur herstellung von 5-h-dibenzo[b,f]azepin oder iminostilben
EP0089417B1 (fr)	1986-02-26	Procédé pour la préparation du phtalide
DD295378A5 (de)	1991-10-31	Stereoselektives hydrierungsverfahren
DE2902542C2 (fr)	1987-11-26
EP0479877B1 (fr)	1994-10-12	Procede de production de n-alkylanilines halogenes
DE3137092C2 (de)	1983-02-03	Verfahren zur Herstellung von Gemischen aus cis- und trans-4-Aminomethyl-cyclohexancarbonsäure in Form der Salze mit bestimmten Mineralsäuren
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DE4336154A1 (de)	1994-04-28	Verfahren zur Herstellung von L-5-(2-Acetoxy-propionyl-amino)-2,4,6-trijod-isophthalsäure-bis-1,3-dihydroxy-polyamid)
DE3441989C2 (fr)	1989-10-19
DE69304581T2 (de)	1997-02-20	Verfahren zur Herstellung von 1,4-Dicyano-2-Buten und ein Katalysator dafür
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EP0789015B1 (fr)	1999-12-29	Procédé pour la préparation d'esters de l'acide N-carboxyméthylanthranilique
EP0634411A1 (fr)	1995-01-18	Procédé de préparation de 8-(4'-(4''-(pyrimidin-2''-yle)-piperazin-1''-yle)-butyle)-8-aza-spiro(4,5)decan-7,9-dione et leur hydrochlorides de haute purété
EP0470375A1 (fr)	1992-02-12	Procédé pour la préparation d'amines aromatiques substitués dans la position p par C1-4 alkoxy
DE2414772C3 (de)	1979-08-30	H33-Diphenylpropyl)-2-methyl-3phenylaziridin und Verfahren zu seiner Herstellung
DE3447070C1 (de)	1986-05-28	Verfahren zur Herstellung von N-Acetyl-4-(aminomethyl-)-cyclohexancarbonsäure-methylester
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