JPS6213956B2 - - Google Patents

Info

Publication number: JPS6213956B2
Authority: JP; Japan
Prior art keywords: urea; carbonyl; methoxy; methylergoline; dimethylaminopropyl
Prior art date: 1980-04-03
Legal status (The legal status 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 status listed.): Expired

Application number

JP56048491A

Other languages

English (en)

Japanese (ja)

Other versions

JPS56156279A (en

Inventor

Saruatei Patorishia

Maria Karauaji Anna

Tenperiiri Arudemio

Bosuisuio Jerumano

Sapini Osuarudo

Dei Sare Enriko

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

FUARUMITARIA KARURO ERUBA SpA

Original Assignee

FUARUMITARIA KARURO ERUBA SpA

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.)

1980-04-03

Filing date

1981-04-02

Publication date

1987-03-30

1981-04-02 Application filed by FUARUMITARIA KARURO ERUBA SpA filed Critical FUARUMITARIA KARURO ERUBA SpA

1981-12-02 Publication of JPS56156279A publication Critical patent/JPS56156279A/ja

1987-03-30 Publication of JPS6213956B2 publication Critical patent/JPS6213956B2/ja

Status Granted legal-status Critical Current

Links

239000004202 carbamide Substances 0.000 claims description 114
150000001875 compounds Chemical class 0.000 claims description 57
238000000034 method Methods 0.000 claims description 31
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 11
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
230000001263 anti-prolactin effect Effects 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
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 class 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 claims description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
125000001183 hydrocarbyl group Chemical group 0.000 claims description 6
150000007522 mineralic acids Chemical class 0.000 claims description 6
150000007524 organic acids Chemical class 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
239000002220 antihypertensive agent Substances 0.000 claims description 3
150000007530 organic bases Chemical class 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
229940030600 antihypertensive agent Drugs 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
239000000010 aprotic solvent Substances 0.000 claims 2
239000003795 chemical substances by application Substances 0.000 claims 2
230000005494 condensation Effects 0.000 claims 1
238000009833 condensation Methods 0.000 claims 1
238000002844 melting Methods 0.000 description 23
230000008018 melting Effects 0.000 description 23
RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 20
BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 12
230000036772 blood pressure Effects 0.000 description 12
230000037396 body weight Effects 0.000 description 12
BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 12
238000011282 treatment Methods 0.000 description 12
230000000694 effects Effects 0.000 description 11
229960002474 hydralazine Drugs 0.000 description 10
SBJSRNIAEBCQDQ-HRBVQNPCSA-N (6ar,10ar)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylic acid Chemical compound C1=CC([C@@H]2[C@H](NCC(C2)C(=O)O)C2)=C3C2=CNC3=C1 SBJSRNIAEBCQDQ-HRBVQNPCSA-N 0.000 description 9
230000003276 anti-hypertensive effect Effects 0.000 description 9
241000700159 Rattus Species 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
238000011156 evaluation Methods 0.000 description 5
230000001988 toxicity Effects 0.000 description 5
231100000419 toxicity Toxicity 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
102000003946 Prolactin Human genes 0.000 description 4
108010057464 Prolactin Proteins 0.000 description 4
239000002253 acid Substances 0.000 description 4
231100000673 dose–response relationship Toxicity 0.000 description 4
IDVWLLCLTVBSCS-UHFFFAOYSA-N n,n'-ditert-butylmethanediimine Chemical compound CC(C)(C)N=C=NC(C)(C)C IDVWLLCLTVBSCS-UHFFFAOYSA-N 0.000 description 4
229940097325 prolactin Drugs 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
CJCSPKMFHVPWAR-JTQLQIEISA-N alpha-methyl-L-dopa Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 CJCSPKMFHVPWAR-JTQLQIEISA-N 0.000 description 3
230000004531 blood pressure lowering effect Effects 0.000 description 3
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 description 3
229960002802 bromocriptine Drugs 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000003814 drug Substances 0.000 description 3
230000000095 emetic effect Effects 0.000 description 3
238000002513 implantation Methods 0.000 description 3
230000003389 potentiating effect Effects 0.000 description 3
229940124597 therapeutic agent Drugs 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
206010020772 Hypertension Diseases 0.000 description 2
206010028980 Neoplasm Diseases 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000036471 bradycardia Effects 0.000 description 2
208000006218 bradycardia Diseases 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229940083181 centrally acting adntiadrenergic agent methyldopa Drugs 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000001177 diphosphate Substances 0.000 description 2
XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 2
235000011180 diphosphates Nutrition 0.000 description 2
239000003480 eluent Substances 0.000 description 2
230000001631 hypertensive effect Effects 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
239000000203 mixture Substances 0.000 description 2
FEKRFYZGYUTGRY-UHFFFAOYSA-N n'-ethylmethanediimine Chemical compound CCN=C=N FEKRFYZGYUTGRY-UHFFFAOYSA-N 0.000 description 2
230000035935 pregnancy Effects 0.000 description 2
230000028327 secretion Effects 0.000 description 2
230000001629 suppression Effects 0.000 description 2
238000005303 weighing Methods 0.000 description 2
YKFCISHFRZHKHY-NGQGLHOPSA-N (2s)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid;trihydrate Chemical compound O.O.O.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 YKFCISHFRZHKHY-NGQGLHOPSA-N 0.000 description 1
FKSLYEKPAMDLFO-XNRPHZJLSA-N (6ar,9r,10ar)-7-propan-2-yl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carboxylic acid Chemical compound C1=CC([C@H]2C[C@H](CN([C@@H]2C2)C(C)C)C(O)=O)=C3C2=CNC3=C1 FKSLYEKPAMDLFO-XNRPHZJLSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
206010000599 Acromegaly Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
208000001287 Galactorrhea Diseases 0.000 description 1
206010017600 Galactorrhoea Diseases 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
208000018737 Parkinson disease Diseases 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 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
150000001718 carbodiimides Chemical class 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000007547 defect Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000019256 formaldehyde Nutrition 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
208000031424 hyperprolactinemia Diseases 0.000 description 1
239000000960 hypophysis hormone Substances 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
208000000509 infertility Diseases 0.000 description 1
230000036512 infertility Effects 0.000 description 1
231100000535 infertility Toxicity 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
NASVTBDJHWPMOO-UHFFFAOYSA-N n,n'-dimethylmethanediimine Chemical compound CN=C=NC NASVTBDJHWPMOO-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000000523 sample Substances 0.000 description 1
238000007127 saponification reaction Methods 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
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 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
- C07D457/04—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 8
- C07D457/06—Lysergic acid amides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP4849181A 1980-04-03 1981-04-02 Ergoline derivative, its manufacture and medicinal composition containing it Granted JPS56156279A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB8011234		1980-04-03

Publications (2)

Publication Number	Publication Date
JPS56156279A JPS56156279A (en)	1981-12-02
JPS6213956B2 true JPS6213956B2 (da)	1987-03-30

Family

ID=10512588

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP4849181A Granted JPS56156279A (en)	1980-04-03	1981-04-02	Ergoline derivative, its manufacture and medicinal composition containing it

Country Status (7)

Country	Link
JP (1)	JPS56156279A (da)
BE (1)	BE888243A (da)
CS (1)	CS221828B2 (da)
HU (1)	HU183382B (da)
SU (1)	SU1053756A3 (da)
UA (1)	UA6027A1 (da)
ZA (1)	ZA812103B (da)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6445652U (da) *	1987-09-16	1989-03-20
JPH01123664U (da) *	1988-02-16	1989-08-23

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2173189B (en) *	1985-02-21	1988-04-27	Maruko Pharmaceutical Co	Ergoline derivatives and salts thereof and pharmaceutical compositions thereof
EP1925616A1 (en) *	2006-10-26	2008-05-28	LEK Pharmaceuticals D.D.	Process for the preparation of crystal forms of cabergoline via stable solvates of cabergoline

1981
- 1981-03-30 ZA ZA00812103A patent/ZA812103B/xx unknown
- 1981-03-31 CS CS812388A patent/CS221828B2/cs unknown
- 1981-04-01 SU SU813263908A patent/SU1053756A3/ru active
- 1981-04-01 UA UA3263908A patent/UA6027A1/uk unknown
- 1981-04-01 HU HU81842A patent/HU183382B/hu unknown
- 1981-04-02 JP JP4849181A patent/JPS56156279A/ja active Granted
- 1981-04-02 BE BE0/204351A patent/BE888243A/fr not_active IP Right Cessation

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6445652U (da) *	1987-09-16	1989-03-20
JPH01123664U (da) *	1988-02-16	1989-08-23

Also Published As

Publication number	Publication date
SU1053756A3 (ru)	1983-11-07
UA6027A1 (uk)	1994-12-29
ZA812103B (en)	1982-04-28
HU183382B (en)	1984-04-28
JPS56156279A (en)	1981-12-02
CS221828B2 (en)	1983-04-29
BE888243A (fr)	1981-10-02

Legal Events

Date	Code	Title	Description
2005-02-08	R250	Receipt of annual fees	Free format text: JAPANESE INTERMEDIATE CODE: R250
2006-01-10	R250	Receipt of annual fees	Free format text: JAPANESE INTERMEDIATE CODE: R250
2006-04-02	EXPY	Cancellation because of completion of term

Publication	Publication Date	Title
US4526892A (en)	1985-07-02	Dimethylaminoalkyl-3-(ergoline-8'βcarbonyl)-ureas
US4797406A (en)	1989-01-10	Amides and esters containing bridged piperidines and use as serotonin M antagonists
EP0618905B1 (en)	1995-10-04	Imidazolyl-alkyl-piperazine and -diazepine derivatives as histamine h3 agonists/antagonists
JPH11501329A (ja)	1999-02-02	ゴナドトロピン放出ホルモン拮抗剤
JPH0717611B2 (ja)	1995-03-01	スピロインダニルカンファースルホニルオキシトシン拮抗剤のアミド置換誘導体
JPS6210519B2 (da)	1987-03-06
EP0423777A2 (en)	1991-04-24	Method of treating gastrointestinal motility disorders
EP0423776A2 (en)	1991-04-24	N-(6)-substituted adenosine compounds
HU203344B (en)	1991-07-29	Process for producing cycloalkylamide derivatives of (8beta)-1-alkyl-6-substituted ergolines
JPS6213956B2 (da)	1987-03-30
EP0121716B1 (de)	1987-12-09	Indolderivate
JPH02218682A (ja)	1990-08-31	エルゴリン誘導体
EP0387603A1 (de)	1990-09-19	Indolderivate
DE3112861C2 (da)	1989-06-01
EP0742214A1 (en)	1996-11-13	Novel seco-D steroids active in the cardiovascular system and pharmaceutical compositions containing same
CS199609B2 (en)	1980-07-31	Method of producing 6-methyl-8-isocyanmethyl ergoline
KR840001473B1 (ko)	1984-09-28	에르골린 유도체의 제조방법
JPH0339513B2 (da)	1991-06-14
KR950014866B1 (ko)	1995-12-16	에르골리닐 헤테로사이클
US3174978A (en)	1965-03-23	Guanyl hydrazones of dialkylaminophenyl lower alkyl ketones
US5633250A (en)	1997-05-27	Imidazoylalkyl substituted with a six or seven membered heterocyclic ring containing two nitrogen atoms
KR910005852B1 (ko)	1991-08-05	이미다조퀴놀린 유도체의 제조방법
GB2074566A (en)	1981-11-04	Ergoline Derivatives
CN108350024B (zh)	2021-04-30	一种取代的甾体类化合物及其应用
US4826840A (en)	1989-05-02	Cerebral protecting agent

JPS6213956B2 - - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (1)

Publications (2)

Family

ID=10512588

Family Applications (1)

Country Status (7)

Cited By (2)

Families Citing this family (2)

Cited By (2)

Also Published As

Similar Documents

Legal Events