CS262670B2 - Process for preparing 2-brom-alfa-ergokryptine - Google Patents

Process for preparing 2-brom-alfa-ergokryptine Download PDF

Info

Publication number: CS262670B2
Authority: CS; Czechoslovakia
Prior art keywords: ergocryptine; bromo; mixture; bromination; hydrogen bromide
Prior art date: 1985-06-12

Application number

CS864358A

Other languages

Czech (cs)

English (en)

Other versions

CS435886A2 (en

Inventor

Gabor Dr Ing Megyeri

Tibor Dr Keve

Janos Dr Ing Galambos

Lajos Ing Kovacs

Bela Stefko

Erik Ing Bogsch

Ferenc Dr Trischler

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.)

1985-06-12

Filing date

1986-06-12

Publication date

1989-03-14

1986-06-12 Application filed by Richter Gedeon Vegyeszet filed Critical Richter Gedeon Vegyeszet

1988-08-16 Publication of CS435886A2 publication Critical patent/CS435886A2/cs

1989-03-14 Publication of CS262670B2 publication Critical patent/CS262670B2/cs

Links

229950001817 alpha-ergocryptine Drugs 0.000 title abstract description 19
238000004519 manufacturing process Methods 0.000 title 1
239000000203 mixture Substances 0.000 claims abstract description 33
OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 claims abstract description 29
238000005893 bromination reaction Methods 0.000 claims abstract description 24
238000000034 method Methods 0.000 claims abstract description 21
230000031709 bromination Effects 0.000 claims abstract description 20
150000003839 salts Chemical class 0.000 claims abstract description 19
239000002253 acid Substances 0.000 claims abstract description 14
YDOTUXAWKBPQJW-NSLWYYNWSA-N alpha-ergocryptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=CNC3=C1 YDOTUXAWKBPQJW-NSLWYYNWSA-N 0.000 claims abstract description 14
238000002360 preparation method Methods 0.000 claims abstract description 9
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 46
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 35
229910000042 hydrogen bromide Inorganic materials 0.000 claims description 23
229960001760 dimethyl sulfoxide Drugs 0.000 claims description 20
239000007858 starting material Substances 0.000 claims description 8
YREISLCRUMOYAY-IIPCNOPRSA-N ergometrine maleate Chemical class OC(=O)\C=C/C(O)=O.C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)C)C2)=C3C2=CNC3=C1 YREISLCRUMOYAY-IIPCNOPRSA-N 0.000 claims description 3
230000035484 reaction time Effects 0.000 claims description 3
YDOTUXAWKBPQJW-UHFFFAOYSA-N alpha-Ergocryptinine Natural products C1=CC(C=2C(N(C)CC(C=2)C(=O)NC2(C(=O)N3C(C(N4CCCC4C3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=CNC3=C1 YDOTUXAWKBPQJW-UHFFFAOYSA-N 0.000 abstract description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 12
KNZORDSJZFOXOV-UHFFFAOYSA-N methylsulfinylmethane;hydrobromide Chemical compound Br.CS(C)=O KNZORDSJZFOXOV-UHFFFAOYSA-N 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
150000001875 compounds Chemical class 0.000 description 10
229930013930 alkaloid Natural products 0.000 description 9
150000003797 alkaloid derivatives Chemical class 0.000 description 9
239000006227 byproduct Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
238000006345 epimerization reaction Methods 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 4
229960003133 ergot alkaloid Drugs 0.000 description 4
238000000746 purification Methods 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
102000003946 Prolactin Human genes 0.000 description 3
108010057464 Prolactin Proteins 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
NOJMTMIRQRDZMT-GSPXQYRGSA-N bromocriptine methanesulfonate Chemical compound CS(O)(=O)=O.C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 NOJMTMIRQRDZMT-GSPXQYRGSA-N 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
229940098779 methanesulfonic acid Drugs 0.000 description 3
150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
239000000047 product Substances 0.000 description 3
229940097325 prolactin Drugs 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
201000000736 Amenorrhea Diseases 0.000 description 2
206010001928 Amenorrhoea Diseases 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
NESVMZOPWPCFAU-UHFFFAOYSA-N Ergoclavinine Natural products C1=CC(C=2C(N(C)CC(C=2)C(=O)NC2(C(=O)N3C(C(N4CCCC4C3(O)O2)=O)CC(C)C)C)C2)=C3C2=CNC3=C1 NESVMZOPWPCFAU-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
208000001287 Galactorrhea Diseases 0.000 description 2
206010017600 Galactorrhoea Diseases 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000003463 adsorbent Substances 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
231100000540 amenorrhea Toxicity 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
NESVMZOPWPCFAU-ZPRCMDFASA-N ergosine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C)C2)=C3C2=CNC3=C1 NESVMZOPWPCFAU-ZPRCMDFASA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
230000035876 healing Effects 0.000 description 2
229940088597 hormone Drugs 0.000 description 2
239000005556 hormone Substances 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000004448 titration Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
GJNCXCPHNRATIQ-UHFFFAOYSA-N 1-bromoazepan-2-one Chemical compound BrN1CCCCCC1=O GJNCXCPHNRATIQ-UHFFFAOYSA-N 0.000 description 1
QRADPXNAURXMSB-UHFFFAOYSA-N 2-bromo-1,1-dioxo-1,2-benzothiazol-3-one Chemical compound C1=CC=C2S(=O)(=O)N(Br)C(=O)C2=C1 QRADPXNAURXMSB-UHFFFAOYSA-N 0.000 description 1
OTVGARFFAAFRAC-UHFFFAOYSA-N 2-bromo-1,4-dioxane Chemical compound BrC1COCCO1 OTVGARFFAAFRAC-UHFFFAOYSA-N 0.000 description 1
MARXMDRWROUXMD-UHFFFAOYSA-N 2-bromoisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(Br)C(=O)C2=C1 MARXMDRWROUXMD-UHFFFAOYSA-N 0.000 description 1
YDOTUXAWKBPQJW-JJANYQHSSA-N 919k69s85n Chemical compound C1=CC(C=2[C@H](N(C)C[C@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=CNC3=C1 YDOTUXAWKBPQJW-JJANYQHSSA-N 0.000 description 1
206010000599 Acromegaly Diseases 0.000 description 1
206010006187 Breast cancer Diseases 0.000 description 1
208000026310 Breast neoplasm Diseases 0.000 description 1
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
208000018737 Parkinson disease Diseases 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
230000004913 activation Effects 0.000 description 1
-1 alkaloid salt Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
238000005352 clarification Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000003291 dopaminomimetic effect Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000003999 initiator Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
CEQFOVLGLXCDCX-WUKNDPDISA-N methyl red Chemical compound C1=CC(N(C)C)=CC=C1\N=N\C1=CC=CC=C1C(O)=O CEQFOVLGLXCDCX-WUKNDPDISA-N 0.000 description 1
HHQJWDKIRXRTLS-UHFFFAOYSA-N n'-bromobutanediamide Chemical compound NC(=O)CCC(=O)NBr HHQJWDKIRXRTLS-UHFFFAOYSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000011148 porous material Substances 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
VFDOIPKMSSDMCV-UHFFFAOYSA-N pyrrolidine;hydrobromide Chemical compound Br.C1CCNC1 VFDOIPKMSSDMCV-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000007420 reactivation Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011833 salt mixture Substances 0.000 description 1
230000028327 secretion Effects 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000002594 sorbent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/02—Ergot alkaloids of the cyclic peptide type
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CS864358A 1985-06-12 1986-06-12 Process for preparing 2-brom-alfa-ergokryptine CS262670B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU852300A HU193317B (en)	1985-06-12	1985-06-12	Process for producing 2-bromo-alpha-ergochristin

Publications (2)

Publication Number	Publication Date
CS435886A2 CS435886A2 (en)	1988-08-16
CS262670B2 true CS262670B2 (en)	1989-03-14

Family

ID=10958743

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS864358A CS262670B2 (en)	1985-06-12	1986-06-12	Process for preparing 2-brom-alfa-ergokryptine

Country Status (13)

Country	Link
US (1)	US4697017A (fr)
JP (1)	JPS61286390A (fr)
BE (1)	BE904897A (fr)
CA (1)	CA1256103A (fr)
CH (1)	CH667092A5 (fr)
CS (1)	CS262670B2 (fr)
DE (1)	DE3619617A1 (fr)
ES (1)	ES8707236A1 (fr)
FR (1)	FR2583419B1 (fr)
GB (1)	GB2176479B (fr)
HU (1)	HU193317B (fr)
IT (1)	IT1191806B (fr)
YU (1)	YU100886A (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU196394B (en) *	1986-06-27	1988-11-28	Richter Gedeon Vegyeszet	Process for preparing 2-halogenated ergoline derivatives
GB9218242D0 (en) *	1992-08-27	1992-10-14	Ici Plc	Chemical process
JPH11507386A (ja) *	1995-06-07	1999-06-29	エルゴ・サイエンス・インコーポレイテッド	哺乳類における新生物疾患を阻害する方法
CN103073387A (zh) *	2013-02-08	2013-05-01	天津师范大学	一种9，10-二溴蒽的制备方法
CN105646547B (zh) *	2014-12-03	2019-05-17	四川海思科制药有限公司	一种甲磺酸溴隐亭化合物

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH507249A (de) *	1968-05-31	1971-05-15	Sandoz Ag	Verfahren zur Herstellung von 2-Brom-a-ergokryptin
CH573431A5 (en) *	1972-06-13	1976-03-15	Sandoz Ag	Dibromo-dihydro-lysergic acid prepn. - by bromination of 9,10-dihydro-lysergic acid in inert solvent, pref. glacial alcoholic or propionic acid
GB1413068A (en) *	1972-06-22	1975-11-05	Farmaceutici Italia	Bromoergolines
DE2656344A1 (de) *	1975-12-23	1977-07-07	Sandoz Ag	Ergolinderivate, ihre verwendung und herstellung
YU216177A (en) *	1977-09-09	1984-02-29	Rudolf Rucman	Process for preparing 2-bromo ergosine
US4609731A (en) *	1979-10-10	1986-09-02	Sandoz Ltd.	Process for brominating ergot alkaloids
DE3101535A1 (de) *	1981-01-14	1982-08-12	Schering Ag, 1000 Berlin Und 4619 Bergkamen	Neue (2-halogen-ergolinyl)-n'.n'-diethyl-harnstoffderivate, verfahren zu ihrer herstellung und deren verwendung als arzneimittel
CH649300A5 (de) *	1981-08-07	1985-05-15	Sandoz Ag	Ergopeptinderivate, ihre herstellung und verwendung.
DE3340025C2 (de) *	1983-11-03	1986-01-09	Schering AG, 1000 Berlin und 4709 Bergkamen	Verfahren zur Herstellung von 2-Brom-8-ergolinyl-Verbindungen

1985
- 1985-06-12 HU HU852300A patent/HU193317B/hu not_active IP Right Cessation
1986
- 1986-05-30 US US06/869,203 patent/US4697017A/en not_active Expired - Fee Related
- 1986-06-10 BE BE0/216763A patent/BE904897A/fr not_active IP Right Cessation
- 1986-06-11 YU YU01008/86A patent/YU100886A/xx unknown
- 1986-06-11 CH CH2364/86A patent/CH667092A5/de not_active IP Right Cessation
- 1986-06-11 IT IT20761/86A patent/IT1191806B/it active
- 1986-06-11 DE DE19863619617 patent/DE3619617A1/de not_active Withdrawn
- 1986-06-11 ES ES555932A patent/ES8707236A1/es not_active Expired
- 1986-06-11 CA CA000511286A patent/CA1256103A/fr not_active Expired
- 1986-06-11 JP JP61133952A patent/JPS61286390A/ja active Pending
- 1986-06-12 GB GB08614342A patent/GB2176479B/en not_active Expired
- 1986-06-12 FR FR868608487A patent/FR2583419B1/fr not_active Expired - Lifetime
- 1986-06-12 CS CS864358A patent/CS262670B2/cs unknown

Also Published As

Publication number	Publication date
BE904897A (fr)	1986-12-10
ES8707236A1 (es)	1987-07-16
US4697017A (en)	1987-09-29
IT8620761A1 (it)	1987-12-11
GB8614342D0 (en)	1986-07-16
IT1191806B (it)	1988-03-23
YU100886A (en)	1988-04-30
HUT40445A (en)	1986-12-28
FR2583419A1 (fr)	1986-12-19
JPS61286390A (ja)	1986-12-16
GB2176479B (en)	1988-12-14
CH667092A5 (de)	1988-09-15
CS435886A2 (en)	1988-08-16
HU193317B (en)	1987-09-28
IT8620761A0 (it)	1986-06-11
ES555932A0 (es)	1987-07-16
GB2176479A (en)	1986-12-31
DE3619617A1 (de)	1986-12-18
CA1256103A (fr)	1989-06-20
FR2583419B1 (fr)	1990-01-12

Publication	Publication Date	Title
SU1528320A3 (ru)	1989-12-07	Способ получени 2-бром- @ -эргокриптина или его кислотно-аддитивных солей
Sundberg et al.	1981	Diels-Alder adducts of 1-benzenesulfonylindole-2-acrylates and 1-(alkoxycarbonyl)-1, 2-dihydropyridines. Intermediates for synthesis of iboga alkaloid analogs
JPH01190680A (ja)	1989-07-31	インドール誘導体およびその製造方法
CS262670B2 (en)	1989-03-14	Process for preparing 2-brom-alfa-ergokryptine
CS247089B2 (en)	1986-11-13	Production method of the 2-bromine-8-ergolinyl compounds
JPS61126082A (ja)	1986-06-13	アミノピロリジン誘導体、そのエステルおよびその塩
EP0251652B1 (fr)	1992-05-20	Dérivés de t-butyl ergoline
JP2663105B2 (ja)	1997-10-15	１４α−ヒドロキシ−４−アンドロステン−３，６，１７−トリオン水和物結晶及びその製造法
FI66185B (fi)	1984-05-31	Nytt foerfarande foer bromering av foereningar
US3239530A (en)	1966-03-08	Process for lysergic acid hydrazides
US3585201A (en)	1971-06-15	10-alkoxy 9,10-dihydro ergoline derivatives
Poliakoff et al.	1973	Synthetic trypanocides. 3. Structure-activity relations
NO873895L (no)	1987-09-16	Indolokinoksaliner med substituenter i 6-stilling som omfatter cykliske grupper.
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