HU183594B - Process for producing 11-methoxy-vincamone - Google Patents

Process for producing 11-methoxy-vincamone Download PDF

Info

Publication number: HU183594B
Authority: HU; Hungary
Prior art keywords: formula; alkali metal; vincamone; methoxy; ome
Prior art date: 1981-09-30

Application number

HU281181A

Other languages

English (en)

Hungarian (hu)

Inventor

Csaba Szantay

Lajos Szabo

Gyoergy Kalaus

Tibor Keve

Janos Galambos

Tibor Acs

Lajos Dancsi

Original Assignee

Richter Gedeon Vegyeszet

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.)

1981-09-30

Filing date

1981-09-30

Publication date

1984-05-28

1981-09-30 Application filed by Richter Gedeon Vegyeszet filed Critical Richter Gedeon Vegyeszet

1981-09-30 Priority to HU281181A priority Critical patent/HU183594B/hu

1982-09-29 Priority to AT360082A priority patent/AT380249B/de

1982-09-29 Priority to GB08227827A priority patent/GB2106908B/en

1982-09-30 Priority to BE0/209138A priority patent/BE894555A/fr

1984-05-28 Publication of HU183594B publication Critical patent/HU183594B/hu

Links

238000000034 method Methods 0.000 title claims abstract description 7
229960002922 vinburnine Drugs 0.000 title description 6
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 7
150000001340 alkali metals Chemical class 0.000 claims abstract description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 6
238000002360 preparation method Methods 0.000 claims abstract description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 3
229910001431 copper ion Inorganic materials 0.000 claims description 3
-1 haloalkyl vincaminic acid ester Chemical class 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
230000003197 catalytic effect Effects 0.000 claims description 2
239000003513 alkali Substances 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 8
239000002253 acid Substances 0.000 abstract description 3
125000000217 alkyl group Chemical group 0.000 abstract description 3
239000003054 catalyst Substances 0.000 abstract description 3
150000002148 esters Chemical class 0.000 abstract description 3
125000004432 carbon atom Chemical group C* 0.000 abstract 2
125000005843 halogen group Chemical group 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
229910021595 Copper(I) iodide Inorganic materials 0.000 description 3
244000309464 bull Species 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 2
238000002955 isolation Methods 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
229960002726 vincamine Drugs 0.000 description 2
229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
WYJAPUKIYAZSEM-MOPGFXCFSA-N Eburnamonine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)CC(=O)N5C2=C1 WYJAPUKIYAZSEM-MOPGFXCFSA-N 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
241000863486 Vinca minor Species 0.000 description 1
229930013930 alkaloid Natural products 0.000 description 1
150000003797 alkaloid derivatives Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000001246 bromo group Chemical group Br* 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
238000001816 cooling Methods 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003951 lactams Chemical class 0.000 description 1
239000010410 layer Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000000203 mixture Substances 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
WYJAPUKIYAZSEM-UHFFFAOYSA-N rac-Eburnamonin Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)CC(=O)N5C2=C1 WYJAPUKIYAZSEM-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000000304 vasodilatating effect Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

HU281181A 1981-09-30 1981-09-30 Process for producing 11-methoxy-vincamone HU183594B (en)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
HU281181A HU183594B (en)	1981-09-30	1981-09-30	Process for producing 11-methoxy-vincamone
AT360082A AT380249B (de)	1981-09-30	1982-09-29	Verfahren zur herstellung von alkoxy-vincamon-derivaten
GB08227827A GB2106908B (en)	1981-09-30	1982-09-29	Alkoxyvincamone derivatives
BE0/209138A BE894555A (fr)	1981-09-30	1982-09-30	Procede de preparation de derives d'alcoxyvincamone et derives ainsi obtenus

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU281181A HU183594B (en)	1981-09-30	1981-09-30	Process for producing 11-methoxy-vincamone

Publications (1)

Publication Number	Publication Date
HU183594B true HU183594B (en)	1984-05-28

Family

ID=10961201

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU281181A HU183594B (en)	1981-09-30	1981-09-30	Process for producing 11-methoxy-vincamone

Country Status (4)

Country	Link
AT (1)	AT380249B (fr)
BE (1)	BE894555A (fr)
GB (1)	GB2106908B (fr)
HU (1)	HU183594B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2623501B1 (fr) *	1987-11-19	1990-03-16	Roussel Uclaf	Nouveaux derives substitues de 20,21-dinoreburnamenine, leur procede de preparation et les nouveaux intermediaires ainsi obtenus, leur application comme medicaments et les compositions pharmaceutiques les renfermant

1981
- 1981-09-30 HU HU281181A patent/HU183594B/hu not_active IP Right Cessation
1982
- 1982-09-29 GB GB08227827A patent/GB2106908B/en not_active Expired
- 1982-09-29 AT AT360082A patent/AT380249B/de not_active IP Right Cessation
- 1982-09-30 BE BE0/209138A patent/BE894555A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
BE894555A (fr)	1983-03-30
GB2106908B (en)	1985-05-30
AT380249B (de)	1986-04-25
ATA360082A (de)	1985-09-15
GB2106908A (en)	1983-04-20

Legal Events

Date	Code	Title	Description
1990-06-28	HU90	Patent valid on 900628
1992-08-28	HMM4	Cancellation of final prot. due to non-payment of fee

Publication	Publication Date	Title
JPH0529216B2 (fr)	1993-04-28
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EP0008831B1 (fr)	1982-03-17	Procédé de préparation de 1-(3-mercapto-2-D-méthyl-propionyl)-L-proline et de ses dérivés
JPS5839822B2 (ja)	1983-09-01	Ｐｇａ型化合物の製法
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HU183594B (en)	1984-05-28	Process for producing 11-methoxy-vincamone
US4042600A (en)	1977-08-16	Pyrolysis of 2-sulfochloride benzoates
FR2510575A1 (fr)	1983-02-04	Nouveaux composes bicycliques, leur procede de preparation et composition pharmaceutique les renfermant
KR980009258A (ko)	1998-04-30	키랄 숙신산 유도체의 제조 방법
FI57586B (fi)	1980-05-30	Foerfarande foer framstaellning av terapeutiskt anvaendbart 1-(2-(beta-naftyloxi)-etyl)-3-metyl-pyrazolon-(5)
US4464534A (en)	1984-08-07	Process for the preparation of vincaminic acid esters
FI88292B (fi)	1993-01-15	Foerfarande foer framstaellning av n-(sulfonylmetyl)formamider
US4329350A (en)	1982-05-11	1,1-Disubstituted octahydro-indolo[2,3-a]quinolizines, process for the preparation thereof and compositions containing same
US4614824A (en)	1986-09-30	Novel apovincaminic acid derivatives
US3932486A (en)	1976-01-13	Substituted tolyl esters of PGA2
US3969464A (en)	1976-07-13	Polycyclic aromatic esters of PGA1
US4058551A (en)	1977-11-15	Substituted phenyl esters of PGA2
US3948970A (en)	1976-04-06	Substituted tolyl esters of PGA1
US4042606A (en)	1977-08-16	Substituted phenyl esters of PGA2
US3931281A (en)	1976-01-06	Substituted anilide ester of PGA2
FR2511677A1 (fr)	1983-02-25	Procede de preparation d'esters des acides alcoxyvincaminiques et alcoxyapovincaminiques
US4012427A (en)	1977-03-15	Substituted phenyl esters of PGE1 -type prostaglandins
US4439363A (en)	1984-03-27	Acetylmethyl ester of hetacyllin and/or salts of this ester
JPS6129351B2 (fr)	1986-07-05