SU493965A3 - Способ получени д-2-замещенных-6-алкил8-замещенных эрголинов - Google Patents

Способ получени д-2-замещенных-6-алкил8-замещенных эрголинов

Info

Publication number: SU493965A3
Authority: SU; USSR - Soviet Union
Prior art keywords: substituted; compound; chloro; cyano; alkyl
Prior art date: 1973-11-28

Application number

SU2004671A

Other languages

English (en)

Russian (ru)

Inventor

Аллен Клеменс Джеймс

Карл Эдмунд

Джеймс Бач Николас

Original Assignee

Эли Лилли Энд Компани (Фирма)

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.)

1973-11-28

Filing date

1974-03-14

Publication date

1975-11-28

1973-11-28 Priority claimed from US419566A external-priority patent/US3920664A/en

1974-03-14 Application filed by Эли Лилли Энд Компани (Фирма) filed Critical Эли Лилли Энд Компани (Фирма)

1975-11-28 Application granted granted Critical

1975-11-28 Publication of SU493965A3 publication Critical patent/SU493965A3/ru

Links

238000000034 method Methods 0.000 title claims description 10
150000001875 compounds Chemical class 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 2
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims description 2
RHGUXDUPXYFCTE-ZWNOBZJWSA-N ergoline Chemical class C1=CC([C@@H]2[C@H](NCCC2)C2)=C3C2=CNC3=C1 RHGUXDUPXYFCTE-ZWNOBZJWSA-N 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims 1
230000017858 demethylation Effects 0.000 claims 1
238000010520 demethylation reaction Methods 0.000 claims 1
238000007069 methylation reaction Methods 0.000 claims 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 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
AWFDCTXCTHGORH-HGHGUNKESA-N 6-[4-[(6ar,9r,10ar)-5-bromo-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carbonyl]piperazin-1-yl]-1-methylpyridin-2-one Chemical compound O=C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC(Br)=C(C=34)C2)C1)C)N(CC1)CCN1C1=CC=CC(=O)N1C AWFDCTXCTHGORH-HGHGUNKESA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
150000003335 secondary amines Chemical class 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000000243 solution Substances 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
125000001188 haloalkyl group Chemical group 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
-1 for example Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000000203 mixture Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 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)

SU2004671A 1973-11-28 1974-03-14 Способ получени д-2-замещенных-6-алкил8-замещенных эрголинов SU493965A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US419566A US3920664A (en)	1972-07-21	1973-11-28	D-2-halo-6-alkyl-8-substituted ergolines and related compounds

Publications (1)

Publication Number	Publication Date
SU493965A3 true SU493965A3 (ru)	1975-11-28

Family

ID=23662805

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU2004671A SU493965A3 (ru)	1973-11-28	1974-03-14	Способ получени д-2-замещенных-6-алкил8-замещенных эрголинов

Country Status (25)

Country	Link
JP (2)	JPS5084598A (cs)
AR (1)	AR212072A1 (cs)
AT (1)	AT333982B (cs)
BE (1)	BE811610R (cs)
BG (1)	BG22399A3 (cs)
CA (1)	CA1011334A (cs)
CH (1)	CH592088A5 (cs)
CS (1)	CS175474B2 (cs)
DD (1)	DD116828A6 (cs)
DE (1)	DE2407904A1 (cs)
DK (1)	DK140480B (cs)
ES (1)	ES423817A1 (cs)
FR (1)	FR2252091B2 (cs)
GB (1)	GB1451724A (cs)
HU (1)	HU169190B (cs)
IE (1)	IE39042B1 (cs)
IL (1)	IL44160A (cs)
NL (1)	NL7402611A (cs)
PH (1)	PH11140A (cs)
PL (1)	PL98288B1 (cs)
RO (1)	RO71304A (cs)
SE (1)	SE416809B (cs)
SU (1)	SU493965A3 (cs)
YU (1)	YU49074A (cs)
ZA (1)	ZA74758B (cs)

Families Citing this family (4)

* 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.
GB0409785D0 (en)	2004-04-30	2004-06-09	Resolution Chemicals Ltd	Preparation of cabergoline
GB0505965D0 (en)	2005-03-23	2005-04-27	Resolution Chemicals Ltd	Preparation of cabergoline
US7339060B2 (en)	2005-03-23	2008-03-04	Resolution Chemicals, Ltd.	Preparation of cabergoline

1973
- 1973-07-16 PH PH15493A patent/PH11140A/en unknown
1974
- 1974-02-05 ZA ZA740758A patent/ZA74758B/xx unknown
- 1974-02-05 GB GB534674A patent/GB1451724A/en not_active Expired
- 1974-02-06 IL IL44160A patent/IL44160A/en unknown
- 1974-02-06 CA CA191,927A patent/CA1011334A/en not_active Expired
- 1974-02-06 IE IE00222/74A patent/IE39042B1/xx unknown
- 1974-02-19 DE DE19742407904 patent/DE2407904A1/de not_active Withdrawn
- 1974-02-22 AT AT146974A patent/AT333982B/de not_active IP Right Cessation
- 1974-02-22 AR AR252504A patent/AR212072A1/es active
- 1974-02-26 NL NL7402611A patent/NL7402611A/xx not_active Application Discontinuation
- 1974-02-26 YU YU00490/74A patent/YU49074A/xx unknown
- 1974-02-27 FR FR7406665A patent/FR2252091B2/fr not_active Expired
- 1974-02-27 BE BE1005751A patent/BE811610R/xx active
- 1974-02-28 DK DK106674AA patent/DK140480B/da unknown
- 1974-02-28 JP JP49022919A patent/JPS5084598A/ja active Pending
- 1974-02-28 CH CH283374A patent/CH592088A5/xx not_active IP Right Cessation
- 1974-02-28 DD DD176871A patent/DD116828A6/xx unknown
- 1974-02-28 SE SE7402672A patent/SE416809B/xx unknown
- 1974-03-01 ES ES423817A patent/ES423817A1/es not_active Expired
- 1974-03-11 PL PL1974169434A patent/PL98288B1/pl unknown
- 1974-03-14 BG BG026052A patent/BG22399A3/xx unknown
- 1974-03-14 HU HUEI533A patent/HU169190B/hu unknown
- 1974-03-14 SU SU2004671A patent/SU493965A3/ru active
- 1974-03-15 RO RO7478047A patent/RO71304A/ro unknown
- 1974-03-15 CS CS1906A patent/CS175474B2/cs unknown
1982
- 1982-10-29 JP JP57190684A patent/JPS5888379A/ja active Pending

Also Published As

Publication number	Publication date
IE39042L (en)	1975-05-28
CH592088A5 (cs)	1977-10-14
RO71304A (ro)	1981-09-24
IL44160A (en)	1977-03-31
FR2252091A2 (cs)	1975-06-20
PH11140A (en)	1977-10-27
BG22399A3 (bg)	1977-02-20
PL98288B1 (pl)	1978-04-29
DK140480B (da)	1979-09-10
DE2407904A1 (de)	1975-06-05
ZA74758B (en)	1974-12-24
FR2252091B2 (cs)	1978-07-28
BE811610R (fr)	1974-08-27
IE39042B1 (en)	1978-07-19
ATA146974A (de)	1976-04-15
AT333982B (de)	1976-12-27
HU169190B (cs)	1976-10-28
SE416809B (sv)	1981-02-09
DK106674A (cs)	1975-07-28
NL7402611A (nl)	1975-05-30
DD116828A6 (cs)	1975-12-12
JPS5888379A (ja)	1983-05-26
GB1451724A (en)	1976-10-06
JPS5084598A (cs)	1975-07-08
ES423817A1 (es)	1976-10-16
DK140480C (cs)	1980-03-03
CS175474B2 (cs)	1977-05-31
AU6531574A (en)	1975-08-07
SE7402672L (cs)	1975-05-29
YU49074A (en)	1982-02-28
AR212072A1 (es)	1978-05-15
CA1011334A (en)	1977-05-31

Publication	Publication Date	Title
US4232157A (en)	1980-11-04	Process for preparing lysergol derivatives
SU493965A3 (ru)	1975-11-28	Способ получени д-2-замещенных-6-алкил8-замещенных эрголинов
SU645581A3 (ru)	1979-01-30	Способ получени -2-галоид-6- метил-8-цианометил или -2-галоид6-метил-8-карбоксамидометилэрголинов
CS231214B1 (en)	1984-10-15	Processing method of 1-substituted n+l8alpha-ergoline+p-n,diethyl urea
DK161646B (da)	1991-07-29	Fremgangsmaade til fremstilling af ergolinderivater og farmaceutisk acceptable salte heraf
CS238601B2 (en)	1985-12-16	Preparation method of o-methylate hydroxyaporphines
US3978085A (en)	1976-08-31	Process for benz[f]-2,5-oxazocines
JPS6284083A (ja)	1987-04-17	ジヒドロリセルグ酸のｎ−アルキル化法
CA1300127C (en)	1992-05-05	Process for preparing lysergol derivatives
US4609731A (en)	1986-09-02	Process for brominating ergot alkaloids
SU417944A3 (ru)	1974-02-28	Способ получения алкалоидов
SU1113006A3 (ru)	1984-09-07	Способ получени транс- @ -октагидро-2 @ -пирроло(3,4- @ )хинолинов или их солей
US4314939A (en)	1982-02-09	Process for the preparation of 15-hydroxyimino-E-homoeburnane and intermediates therefor
GB2039892A (en)	1980-08-20	Production of narwedine-type derivatives
US3583992A (en)	1971-06-08	1-methyl-d-lysergic acid-dihydroxy-alkyl-amides
US3833667A (en)	1974-09-03	Process for the preparation of 1,2-di-(o-or p-nitrophenyl)-ethanol
SU563915A3 (ru)	1977-06-30	Способ получени 2-оксиметил3-фенил-4/3н/-хиназолинона или его соли
CA1097652A (en)	1981-03-17	Eprimerization process
SU528870A3 (ru)	1976-09-15	Способ получени производных 2-имидазолидинона или их солей
SU423299A3 (ru)	1974-04-05	Способ получения производных тетрлгидробензодиазепинонл
GB2165845A (en)	1986-04-23	Dioxinopyridine derivatives
SU437294A1 (ru)	1974-07-25	Способ получени производных 2-амино-дигидро-бензодиазепинона
US4189444A (en)	1980-02-19	Process for the preparation of N,N'-disubstituted 2-naphthaleneethanimidamide and intermediates used therein
US3625948A (en)	1971-12-07	Process for the preparation of hexahydromethanobenzazocines
FI66382B (fi)	1984-06-29	Foerfarande foer framstaellning av farmaceutiskt anvaendbar 17,17's-bisspartein