CH619465A5 - - Google Patents

Download PDF

Info

Publication number: CH619465A5
Authority: CH; Switzerland
Prior art keywords: methyl; compound; formula; ergoline; prolactin
Prior art date: 1974-12-06

Application number

CH1580175A

Other languages

German (de)

English (en)

Inventor

Edmund Carl Kornfeld

Nicholas James Bach

Original Assignee

Lilly Co Eli

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.)

1974-12-06

Filing date

1975-12-04

Publication date

1980-09-30

1975-12-04 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1980-09-30 Publication of CH619465A5 publication Critical patent/CH619465A5/de

Links

150000001875 compounds Chemical class 0.000 claims description 25
102000003946 Prolactin Human genes 0.000 claims description 16
108010057464 Prolactin Proteins 0.000 claims description 16
229940097325 prolactin Drugs 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 12
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 9
150000003839 salts Chemical class 0.000 claims description 9
238000000034 method Methods 0.000 claims description 7
229960003133 ergot alkaloid Drugs 0.000 claims description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 5
238000011282 treatment Methods 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 4
230000000694 effects Effects 0.000 claims description 4
230000002140 halogenating effect Effects 0.000 claims description 4
231100000252 nontoxic Toxicity 0.000 claims description 4
230000003000 nontoxic effect Effects 0.000 claims description 4
230000001419 dependent effect Effects 0.000 claims description 2
230000002411 adverse Effects 0.000 claims 1
150000001408 amides Chemical class 0.000 claims 1
230000008021 deposition Effects 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 claims 1
241000700159 Rattus Species 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000002904 solvent Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
229940123796 Prolactin inhibitor Drugs 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
230000028327 secretion Effects 0.000 description 3
239000000243 solution Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 2
OEEOVQRAKKPOQU-SGIREYDYSA-N (6aR,9R,10aR)-9-(isocyanomethyl)-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline Chemical compound CN1C[C@@H](C[C@@H]2C=3C=CC=C4NC=C(C[C@@H]12)C34)C[N+]#[C-] OEEOVQRAKKPOQU-SGIREYDYSA-N 0.000 description 2
XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 2
-1 6-methyl-8β-isocyano-methylergoline Chemical compound 0.000 description 2
206010063928 Amenorrhoea-galactorrhoea syndrome Diseases 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 2
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
201000000079 gynecomastia Diseases 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
210000002307 prostate Anatomy 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 2
229960003147 reserpine Drugs 0.000 description 2
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 2
210000002966 serum Anatomy 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
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 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
QVRCMEVTUIOJFP-OJDRRSAWSA-N (6aR,10aR)-9-isocyano-9-methyl-6,6a,7,8,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline Chemical compound [N+](#[C-])C1(CN[C@@H]2CC3=CNC4=CC=CC([C@H]2C1)=C34)C QVRCMEVTUIOJFP-OJDRRSAWSA-N 0.000 description 1
FGBDDLRAORVDCA-SKNXHYNKSA-N (6ar,10ar)-9-(isocyanomethyl)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline Chemical compound C1=CC([C@@H]2[C@H](NCC(C2)C[N+]#[C-])C2)=C3C2=CNC3=C1 FGBDDLRAORVDCA-SKNXHYNKSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
206010006187 Breast cancer Diseases 0.000 description 1
208000026310 Breast neoplasm Diseases 0.000 description 1
208000004054 Chiari-Frommel Syndrome Diseases 0.000 description 1
208000001287 Galactorrhea Diseases 0.000 description 1
206010017600 Galactorrhoea Diseases 0.000 description 1
206010020880 Hypertrophy Diseases 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
206010054107 Nodule Diseases 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
208000004350 Strabismus Diseases 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
ODTCIYCTILPXFR-NTVGDFDMSA-N [(6ar,10ar)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-yl]methanamine Chemical compound C1=CC([C@@H]2[C@H](NCC(C2)CN)C2)=C3C2=CNC3=C1 ODTCIYCTILPXFR-NTVGDFDMSA-N 0.000 description 1
208000023599 acquired hyperprolactinemia Diseases 0.000 description 1
208000009956 adenocarcinoma Diseases 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000037396 body weight Effects 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
230000008195 breast development Effects 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
OSQPUMRCKZAIOZ-UHFFFAOYSA-N carbon dioxide;ethanol Chemical compound CCO.O=C=O OSQPUMRCKZAIOZ-UHFFFAOYSA-N 0.000 description 1
239000000969 carrier Substances 0.000 description 1
RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 1
229960002327 chloral hydrate Drugs 0.000 description 1
ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
229960001076 chlorpromazine Drugs 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
229940011871 estrogen Drugs 0.000 description 1
239000000262 estrogen Substances 0.000 description 1
239000000284 extract Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
208000031424 hyperprolactinemia Diseases 0.000 description 1
201000006316 hypertropia Diseases 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
150000002527 isonitriles Chemical class 0.000 description 1
230000006651 lactation Effects 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
239000011707 mineral Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
201000002140 prolactin producing pituitary tumor Diseases 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
229940001470 psychoactive drug Drugs 0.000 description 1
239000004089 psychotropic agent Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
238000005303 weighing Methods 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Diabetes (AREA)
Endocrinology (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)

CH1580175A 1974-12-06 1975-12-04 CH619465A5 (fi)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/530,318 US3985752A (en)	1974-12-06	1974-12-06	6-Methyl-8-(substituted) methylergolines

Publications (1)

Publication Number	Publication Date
CH619465A5 true CH619465A5 (fi)	1980-09-30

Family

ID=24113213

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH1580175A CH619465A5 (fi)	1974-12-06	1975-12-04
CH1580275A CH617197A5 (fi)	1974-12-06	1975-12-04

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH1580275A CH617197A5 (fi)	1974-12-06	1975-12-04

Country Status (29)

Country	Link
US (1)	US3985752A (fi)
JP (2)	JPS5946235B2 (fi)
AR (2)	AR207664A1 (fi)
AT (2)	AT348141B (fi)
AU (1)	AU498226B2 (fi)
BE (1)	BE836308A (fi)
BG (3)	BG33435A3 (fi)
CA (2)	CA1062253A (fi)
CH (2)	CH619465A5 (fi)
CS (2)	CS199609B2 (fi)
DD (2)	DD123749A5 (fi)
DE (1)	DE2554000A1 (fi)
DK (2)	DK547675A (fi)
ES (3)	ES443275A1 (fi)
FR (1)	FR2293203A1 (fi)
GB (1)	GB1526835A (fi)
GR (2)	GR60026B (fi)
HU (3)	HU173724B (fi)
IE (1)	IE42372B1 (fi)
IL (1)	IL48573A (fi)
MX (1)	MX3113E (fi)
NL (1)	NL7514058A (fi)
PH (1)	PH12630A (fi)
PL (3)	PL102198B1 (fi)
RO (2)	RO65456A (fi)
SE (2)	SE421423B (fi)
SU (3)	SU685155A3 (fi)
YU (2)	YU304775A (fi)
ZA (1)	ZA757624B (fi)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4166182A (en) *	1978-02-08	1979-08-28	Eli Lilly And Company	6-n-propyl-8-methoxymethyl or methylmercaptomethylergolines and related compounds
AU526764B2 (en) *	1978-09-08	1983-01-27	Farmitalia Carlo Erba S.P.A.	Ergoline derivatives
HU180467B (en) *	1979-07-12	1983-03-28	Gyogyszerkutato Intezet	Process for producing new ergol-8-ene- and ergoline-sceleted compounds
US4683313A (en) *	1985-06-24	1987-07-28	Eli Lilly And Company	2-alkyl(or phenyl)thio-6-N alkyl ergolines and 4-dialkylaminotetrahydrobenz[c,d]indoles
JPH0541005Y2 (fi) *	1987-07-14	1993-10-18
JPH02174820A (ja) *	1988-12-27	1990-07-06	Sekisui Chem Co Ltd	トイレット
AU2635599A (en) *	1999-03-17	2000-10-04	Eugen Eigenmann	Use of prolactin inhibitors for the treatment of fertility problems in animal species
US20070243240A9 (en) *	2000-08-24	2007-10-18	Fred Windt-Hanke	Transdermal therapeutic system

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL28388A (en) *	1966-07-29	1971-11-29	Farma Italia Soc	History 1, 6 - Dimethyl - A 01 - Argolin
CH507248A (de) *	1967-03-16	1971-05-15	Spofa Vereinigte Pharma Werke	Verfahren zur Herstellung von D-6-Methylergolin(I)ylessigsäure

1974
- 1974-12-06 US US05/530,318 patent/US3985752A/en not_active Expired - Lifetime
1975
- 1975-01-01 AR AR261511A patent/AR207664A1/es active
- 1975-01-01 AR AR261512A patent/AR208104A1/es active
- 1975-11-20 CS CS757860A patent/CS199609B2/cs unknown
- 1975-11-20 CS CS757859A patent/CS200483B2/cs unknown
- 1975-11-27 GB GB48901/75A patent/GB1526835A/en not_active Expired
- 1975-11-28 GR GR49484A patent/GR60026B/el unknown
- 1975-11-28 PH PH17816A patent/PH12630A/en unknown
- 1975-11-28 MX MX004193U patent/MX3113E/es unknown
- 1975-11-28 GR GR49483A patent/GR60025B/el unknown
- 1975-11-30 IL IL48573A patent/IL48573A/xx unknown
- 1975-12-01 DE DE19752554000 patent/DE2554000A1/de not_active Withdrawn
- 1975-12-02 CA CA240,916A patent/CA1062253A/en not_active Expired
- 1975-12-02 AU AU87182/75A patent/AU498226B2/en not_active Expired
- 1975-12-02 NL NL7514058A patent/NL7514058A/xx not_active Application Discontinuation
- 1975-12-02 CA CA240,915A patent/CA1062252A/en not_active Expired
- 1975-12-03 SE SE7513641A patent/SE421423B/xx not_active IP Right Cessation
- 1975-12-03 YU YU03047/75A patent/YU304775A/xx unknown
- 1975-12-03 JP JP50144581A patent/JPS5946235B2/ja not_active Expired
- 1975-12-03 SE SE7513640A patent/SE421422B/xx not_active IP Right Cessation
- 1975-12-03 YU YU03048/75A patent/YU304875A/xx unknown
- 1975-12-04 PL PL1975185225A patent/PL102198B1/pl unknown
- 1975-12-04 RO RO7584088A patent/RO65456A/ro unknown
- 1975-12-04 PL PL1975185226A patent/PL102195B1/pl unknown
- 1975-12-04 SU SU752194455A patent/SU685155A3/ru active
- 1975-12-04 FR FR7537117A patent/FR2293203A1/fr active Granted
- 1975-12-04 SU SU752194702A patent/SU694075A3/ru active
- 1975-12-04 HU HU75EI657A patent/HU173724B/hu unknown
- 1975-12-04 RO RO7584087A patent/RO64281A/ro unknown
- 1975-12-04 CH CH1580175A patent/CH619465A5/de not_active IP Right Cessation
- 1975-12-04 DK DK547675A patent/DK547675A/da unknown
- 1975-12-04 HU HU75EI848A patent/HU175228B/hu unknown
- 1975-12-04 PL PL1975208580A patent/PL106884B1/pl unknown
- 1975-12-04 DK DK547575AA patent/DK142321B/da not_active IP Right Cessation
- 1975-12-04 CH CH1580275A patent/CH617197A5/de not_active IP Right Cessation
- 1975-12-04 ZA ZA757624A patent/ZA757624B/xx unknown
- 1975-12-04 HU HUEI000658 patent/HU173847B/hu unknown
- 1975-12-05 DD DD189913A patent/DD123749A5/xx unknown
- 1975-12-05 BG BG033760A patent/BG33435A3/xx not_active Expired
- 1975-12-05 AT AT927875A patent/AT348141B/de not_active IP Right Cessation
- 1975-12-05 ES ES443275A patent/ES443275A1/es not_active Expired
- 1975-12-05 ES ES443276A patent/ES443276A1/es not_active Expired
- 1975-12-05 BG BG031706A patent/BG33288A3/xx unknown
- 1975-12-05 IE IE2657/75A patent/IE42372B1/en unknown
- 1975-12-05 BE BE1007062A patent/BE836308A/xx not_active IP Right Cessation
- 1975-12-05 BG BG031705A patent/BG33287A3/xx unknown
- 1975-12-05 DD DD189914A patent/DD123748A5/xx unknown
- 1975-12-05 AT AT927975A patent/AT347050B/de not_active IP Right Cessation
1976
- 1976-07-12 SU SU762379565A patent/SU724085A3/ru active
1977
- 1977-04-11 ES ES457709A patent/ES457709A1/es not_active Expired
1984
- 1984-04-24 JP JP59083605A patent/JPS6017795B2/ja not_active Expired

Also Published As

Publication number	Publication date
YU304775A (en)	1982-02-28
DK547675A (da)	1976-06-07
BG33288A3 (en)	1983-01-14
BG33287A3 (en)	1983-01-14
SE421422B (sv)	1981-12-21
FR2293203B1 (fi)	1978-07-28
AR208104A1 (es)	1976-11-30
ATA927975A (de)	1978-04-15
GR60025B (en)	1978-03-31
DE2554000A1 (de)	1976-06-16
ZA757624B (en)	1977-07-27
SU724085A3 (ru)	1980-03-25
SE421423B (sv)	1981-12-21
PL102198B1 (pl)	1979-03-31
DK142321C (fi)	1981-03-09
IE42372L (en)	1976-06-06
PL102195B1 (pl)	1979-03-31
AU498226B2 (en)	1979-02-22
DD123749A5 (fi)	1977-01-12
USB530318I5 (fi)	1976-01-13
ES443276A1 (es)	1977-08-16
JPS59210085A (ja)	1984-11-28
CS200483B2 (en)	1980-09-15
JPS5182300A (fi)	1976-07-19
CA1062252A (en)	1979-09-11
SU685155A3 (ru)	1979-09-05
MX3113E (es)	1980-04-18
RO65456A (ro)	1980-01-15
AU8718275A (en)	1977-06-09
JPS5946235B2 (ja)	1984-11-10
GB1526835A (en)	1978-10-04
YU304875A (en)	1982-02-28
ES443275A1 (es)	1977-09-16
HU173847B (hu)	1979-09-28
AT347050B (de)	1978-12-11
NL7514058A (nl)	1976-06-09
PH12630A (en)	1979-07-05
CH617197A5 (fi)	1980-05-14
FR2293203A1 (fr)	1976-07-02
AT348141B (de)	1979-01-25
DK547575A (fi)	1976-06-07
HU173724B (hu)	1979-07-28
BE836308A (fr)	1976-06-08
US3985752A (en)	1976-10-12
DD123748A5 (fi)	1977-01-12
JPS6017795B2 (ja)	1985-05-07
SE7513641L (sv)	1976-06-08
CA1062253A (en)	1979-09-11
HU175228B (hu)	1980-06-28
GR60026B (en)	1978-03-31
AR207664A1 (es)	1976-10-22
RO64281A (fr)	1979-07-15
ES457709A1 (es)	1978-03-01
SE7513640L (sv)	1976-06-08
CS199609B2 (en)	1980-07-31
IL48573A0 (en)	1976-01-30
BG33435A3 (en)	1983-02-15
SU694075A3 (ru)	1979-10-25
IL48573A (en)	1979-03-12
ATA927875A (de)	1978-06-15
DK142321B (da)	1980-10-13
PL106884B1 (pl)	1980-01-31
IE42372B1 (en)	1980-07-30

Publication	Publication Date	Title
DE1695556C3 (de)	1981-06-25	3-Alkyl-1,2,3,4,4a,9-hexahydropyrazino[1,2-f]morphanthridinderivate
DE69716062T2 (de)	2003-06-18	Benzofuran-derivate und deren verwendung
DD141928A5 (de)	1980-05-28	Verfahren zur herstellung neuer ergolinderivate
WO1980000152A1 (en)	1980-02-07	3-aminopropoxy-aryl derivates,preparation and use thereof
DE3525564A1 (de)	1987-02-05	Tricyclische verbindungen mit indolstruktur, verfahren zu ihrer herstellung und deren verwendung als arzneimittel
DE3200304A1 (de)	1982-08-26	3-aminopropoxyaryl-derivate, ihre herstellung und sie enthaltende arzneimittel
DE2300107C2 (de)	1982-03-11	Vitamin A-Säureanilid-4-carbonsäureäthylester, Verfahren zu seiner Herstellung und diesen enthaltende Zubereitungen
EP0528922A1 (de)	1993-03-03	Neue sulfonylverbindungen
CH617196A5 (fi)	1980-05-14
DE2407115B2 (de)	1979-08-09	2,6-Dimethyl-l,4-dihydropyridin-3carbonsäureamino-alkylesterderivate, Verfahren zu ihrer Herstellung sowie ihre Verwendung
DE69101330T2 (de)	1994-06-16	Mit einem heterocyclischen Ring substituierte Cycloalkano[b]dihydroindole und -indolsulfonamide.
CH619465A5 (fi)	1980-09-30
DE2928187A1 (de)	1980-01-24	Optisch aktive oder racemische brom- 14-oxo-e-homoeburnanderivate, verfahren zur herstellung derselben und von optisch aktiven oder racemischen 11-bromvincaminsaeureesterderivaten und optisch aktive oder racemische 11-bromvincaminsaeureesterderivate sowie erstere oder letztere enthaltende arzneimittel
DE2302866A1 (de)	1973-08-02	Neue 1-substituierte-1,4-dihydropyridinderivate
DE2554629A1 (de)	1976-06-10	8,8-disubstituierte-6-methylergoline
EP0705830A1 (de)	1996-04-10	2,3-Cyclisch kondensierte 1,4-Dihydropyridine, Verfahren zu ihrer Herstellung und ihre Verwendung als selektive Kaliumkanalmodulatoren
DE3118521A1 (de)	1982-12-02	Dibenzo(de,g)chinolin-derivate, verfahren zu deren herstellung und deren verwendung bei der bekaempfung von erkaeltungskrankheiten und allergien
EP0665228A1 (de)	1995-08-02	Neue 3-Phenylsulfonyl-3,7-diazabicyclo(3,3,1)nonan-Verbindungen enthaltende Arzneimittel
EP0473963A1 (de)	1992-03-11	Neue Pyrrolobenzimidazole, Imidazobenzoxazinone und Imidazochinolone, Verfahren zu ihrer Herstellung und ihre Verwendung sowie die Verbindungen enthaltende Zubereitungen
DE2601473A1 (de)	1976-07-22	2,3-dihydroergoline und verfahren zu ihrer herstellung
EP0665014B1 (de)	1997-09-03	3-Benzoyl-3,7-diazabicyclo(3,3,1)nonan-Verbindungen mit anti-arrhythmischer Wirkung
DE2335750A1 (de)	1974-02-14	D-6-methyl-2,8-disubst.-ergoline
EP0045911B1 (de)	1983-12-14	Neue Aminopropanol-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
EP0180833B1 (de)	1989-07-19	4-Oxo-pyrido[2,3]pyrimidin-Derivate, Verfahren zur deren Herstellung und diese ethaltende Arzneimittel
DD144671A5 (de)	1980-10-29	Verfahren zur herstellung von 2-azaergolinen und 2-aza-8(oder 9)ergolenen

Legal Events

Date	Code	Title	Description
1988-08-31	PL	Patent ceased
2024-10-31	PL	Patent ceased