DD142713A1 - Verfahren zur herstellung von lysergol-derivaten - Google Patents

Verfahren zur herstellung von lysergol-derivaten Download PDF

Info

Publication number: DD142713A1
Authority: DD; German Democratic Republic
Prior art keywords: formula; lysergol; methyl; reaction; alpha
Prior art date: 1978-04-05

Application number

DD79212043A

Other languages

German (de)

English (en)

Inventor

Enrico C Mora

Original Assignee

Mora E C

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.)

1978-04-05

Filing date

1979-04-05

Publication date

1980-07-09

1979-04-05 Application filed by Mora E C filed Critical Mora E C

1980-07-09 Publication of DD142713A1 publication Critical patent/DD142713A1/de

Links

BIXJFIJYBLJTMK-MEBBXXQBSA-N lysergol Chemical class C1=CC(C2=C[C@@H](CO)CN([C@@H]2C2)C)=C3C2=CNC3=C1 BIXJFIJYBLJTMK-MEBBXXQBSA-N 0.000 title claims description 15
238000004519 manufacturing process Methods 0.000 title 1
238000000034 method Methods 0.000 claims description 15
150000001875 compounds Chemical class 0.000 claims description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
BIXJFIJYBLJTMK-UHFFFAOYSA-N Lysergol Natural products C1=CC(C2=CC(CO)CN(C2C2)C)=C3C2=CNC3=C1 BIXJFIJYBLJTMK-UHFFFAOYSA-N 0.000 claims description 8
238000005886 esterification reaction Methods 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
-1 heterocyclic carboxylic acids Chemical class 0.000 claims description 6
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
DXGTUUQHTDOFFQ-UHFFFAOYSA-N [N].C1=CC=C2NC=CC2=C1 Chemical group [N].C1=CC=C2NC=CC2=C1 DXGTUUQHTDOFFQ-UHFFFAOYSA-N 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
239000011261 inert gas Substances 0.000 claims description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 3
238000007069 methylation reaction Methods 0.000 claims description 3
125000001931 aliphatic group Chemical group 0.000 claims description 2
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 2
229910052753 mercury Inorganic materials 0.000 claims description 2
239000012022 methylating agents‎ Substances 0.000 claims description 2
238000006552 photochemical reaction Methods 0.000 claims description 2
239000002904 solvent Substances 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 description 17
239000000243 solution Substances 0.000 description 8
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
150000001735 carboxylic acids Chemical class 0.000 description 5
230000032050 esterification Effects 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
235000001968 nicotinic acid Nutrition 0.000 description 4
239000011664 nicotinic acid Substances 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
ZAGRKAFMISFKIO-UHFFFAOYSA-N Isolysergic acid Natural products C1=CC(C2=CC(CN(C2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000011084 recovery Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 2
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
FQIUCPGDKPXSLL-UHFFFAOYSA-N 5-bromopyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC(Br)=C1 FQIUCPGDKPXSLL-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000005457 ice water Substances 0.000 description 2
230000001678 irradiating effect Effects 0.000 description 2
FSIZNIXUPRQTLZ-QMTHXVAHSA-N lysergic acid Chemical compound C1=CC=C2C3=C[C@@H](C(O)=O)CN(C)[C@@H]3CC3=CN=C1[C]32 FSIZNIXUPRQTLZ-QMTHXVAHSA-N 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
229960003512 nicotinic acid Drugs 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
101100501713 Caenorhabditis elegans ergo-1 gene Proteins 0.000 description 1
241000207783 Ipomoea Species 0.000 description 1
229910010082 LiAlH Inorganic materials 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
230000002908 adrenolytic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000001348 alkyl chlorides Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000001035 methylating effect Effects 0.000 description 1
230000011987 methylation Effects 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
150000003254 radicals Chemical group 0.000 description 1
239000002994 raw material Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 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)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD79212043A 1978-04-05 1979-04-05 Verfahren zur herstellung von lysergol-derivaten DD142713A1 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT22011/78A IT1094965B (it)	1978-04-05	1978-04-05	Procedimento di preparazione di derivati del lisergolo

Publications (1)

Publication Number	Publication Date
DD142713A1 true DD142713A1 (de)	1980-07-09

Family

ID=11190149

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79212043A DD142713A1 (de)	1978-04-05	1979-04-05	Verfahren zur herstellung von lysergol-derivaten

Country Status (21)

Country	Link
US (1)	US4232157A (da)
EP (1)	EP0004664B1 (da)
AT (1)	AT369366B (da)
AU (1)	AU530864B2 (da)
CA (1)	CA1124713A (da)
DD (1)	DD142713A1 (da)
DE (1)	DE2962494D1 (da)
DK (1)	DK148259C (da)
ES (1)	ES476725A1 (da)
FI (1)	FI66376C (da)
FR (1)	FR2421901A1 (da)
GB (1)	GB2018245B (da)
GR (1)	GR66982B (da)
HU (1)	HU177591B (da)
IT (1)	IT1094965B (da)
NO (1)	NO150799C (da)
PL (1)	PL115244B1 (da)
PT (1)	PT69426A (da)
SU (1)	SU884572A3 (da)
YU (1)	YU41151B (da)
ZA (1)	ZA791609B (da)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4382940A (en) *	1979-12-06	1983-05-10	Farmitalia Carlo Erba S.P.A.	Ercoline derivatives and therapeutic compositions having CNS affecting activity
IT1173489B (it) *	1984-03-27	1987-06-24	Inverni Della Beffa Spa	Procedimento di preparazione di 1-metil-10alfa-metossilumilisergolo e di suci esteri,e intermedi per la loro preparazione
IT1213206B (it) *	1984-08-07	1989-12-14	Inverni Della Beffa Spa	Procedimento per la preparazione di derivati del lisergolo.
HU193782B (en) *	1985-06-21	1987-11-30	Richter Gedeon Vegyeszet	Process for producing 2-halogeno-nicergoline derivatives and acid additional salts thereof
HU193781B (en) *	1985-06-21	1987-11-30	Richter Gedeon Vegyeszet	Process for producing 10alpha-methoxy-6-methylergoline derivatives and acid additional salts thereof
FR2584719B1 (fr) *	1985-07-11	1987-10-02	Rhone Poulenc Sante	Procede de preparation des derives n-methyles du lysergol et du methoxy-10a lumilysergol
FR2584721B1 (fr) *	1985-07-11	1987-10-02	Rhone Poulenc Sante	Procede de preparation des derives n-methyles du dihydrolysergate de methyle ou du methoxylumilysergate de methyle
FR2584720B1 (fr) *	1985-07-11	1987-10-02	Rhone Poulenc Sante	Procede de preparation de derives n-methyles de l'ergoline
CH674367A5 (da) *	1987-06-16	1990-05-31	Arysearch Arylan Ag
US5120784A (en) *	1988-09-01	1992-06-09	Basf Aktiengesellschaft	Heat-resistant thermoplastic molding compositions
US6060483A (en) *	1996-06-27	2000-05-09	Pharmacia & Upjohn S.P.A.	Antineurodegenerative ergoline derivatives
FR2786099B1 (fr)	1998-11-24	2000-12-29	Aventis Laboratoire	Nouvelle application therapeutique de la 1,6-dimethyl-8beta- hydroxymethyl-10alpha-methoxyergoline
CN111116580B (zh) *	2019-12-27	2022-08-23	上海应用技术大学	一种尼麦角林的改进制备方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3228943A (en) *	1962-06-11	1966-01-11		Lumilysergol derivatives
ES290275A2 (es) *	1962-07-26	1964-03-01	Farm Italia	Procedimiento para preparar nuevos compuestos de la 6-metil y la 1,6-dimetil-er-golina ii
US3879554A (en) *	1970-03-20	1975-04-22	Farmaceutici Italia	Use of 1,6-dimethyl-8-{62 -(5-bromonicotinoyloxymethyl)-10 {60 -methoxyergoline in treating cerebral and peripheral metabolic vascular disorders
NL7102982A (da) *	1970-03-20	1971-09-22	Farmaceutici Italia
NL159384B (nl) *	1971-03-13	1979-02-15	Farmaceutici Italia	Werkwijze voor het bereiden van een geneesmiddel met een adrenolytische activiteit, alsmede werkwijze voor het bereiden van een ester van 1-methyl-10-methoxylumilysergol.
YU39278B (en) *	1976-12-22	1984-10-31	Lek Tovarna Farmacevtskih	Process for preparing 5-bromo nicotinic acid esters

1978
- 1978-04-05 IT IT22011/78A patent/IT1094965B/it active
1979
- 1979-01-10 ES ES476725A patent/ES476725A1/es not_active Expired
- 1979-03-30 GR GR58730A patent/GR66982B/el unknown
- 1979-04-02 PT PT69426A patent/PT69426A/pt unknown
- 1979-04-03 HU HU79CO367A patent/HU177591B/hu unknown
- 1979-04-03 AT AT0246679A patent/AT369366B/de not_active IP Right Cessation
- 1979-04-03 US US06/026,685 patent/US4232157A/en not_active Expired - Lifetime
- 1979-04-03 EP EP79101015A patent/EP0004664B1/en not_active Expired
- 1979-04-03 DE DE7979101015T patent/DE2962494D1/de not_active Expired
- 1979-04-04 YU YU801/79A patent/YU41151B/xx unknown
- 1979-04-04 AU AU45713/79A patent/AU530864B2/en not_active Ceased
- 1979-04-04 SU SU792748500A patent/SU884572A3/ru active
- 1979-04-04 GB GB7911834A patent/GB2018245B/en not_active Expired
- 1979-04-04 FI FI791110A patent/FI66376C/fi not_active IP Right Cessation
- 1979-04-04 ZA ZA791609A patent/ZA791609B/xx unknown
- 1979-04-04 DK DK138879A patent/DK148259C/da not_active IP Right Cessation
- 1979-04-04 CA CA324,886A patent/CA1124713A/en not_active Expired
- 1979-04-04 NO NO791139A patent/NO150799C/no unknown
- 1979-04-05 FR FR7908608A patent/FR2421901A1/fr active Granted
- 1979-04-05 PL PL1979214713A patent/PL115244B1/pl unknown
- 1979-04-05 DD DD79212043A patent/DD142713A1/de unknown

Also Published As

Publication number	Publication date
EP0004664B1 (en)	1982-04-14
GR66982B (da)	1981-05-15
ES476725A1 (es)	1979-12-16
ZA791609B (en)	1980-04-30
DK148259B (da)	1985-05-20
NO791139L (no)	1979-10-08
GB2018245A (en)	1979-10-17
DE2962494D1 (en)	1982-05-27
AU530864B2 (en)	1983-08-04
IT7822011A0 (it)	1978-04-05
US4232157A (en)	1980-11-04
ATA246679A (de)	1982-05-15
PL214713A1 (da)	1980-01-02
SU884572A3 (ru)	1981-11-23
FI66376B (fi)	1984-06-29
HU177591B (en)	1981-11-28
NO150799B (no)	1984-09-10
NO150799C (no)	1984-12-27
YU80179A (en)	1983-02-28
DK148259C (da)	1985-10-14
FR2421901A1 (fr)	1979-11-02
AT369366B (de)	1982-12-27
PL115244B1 (en)	1981-03-31
CA1124713A (en)	1982-06-01
GB2018245B (en)	1982-09-02
FI66376C (fi)	1984-10-10
AU4571379A (en)	1979-11-01
FI791110A7 (fi)	1979-10-06
YU41151B (en)	1986-12-31
IT1094965B (it)	1985-08-10
FR2421901B1 (da)	1983-07-22
EP0004664A1 (en)	1979-10-17
DK138879A (da)	1979-10-06
PT69426A (en)	1979-05-01

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