SE439163B - 8beta-hydrozinometyl-ergolin-derivat och farmaceutisk beredning derav - Google Patents

8beta-hydrozinometyl-ergolin-derivat och farmaceutisk beredning derav

Info

Publication number: SE439163B
Authority: SE; Sweden
Prior art keywords: methyl; group; ergoline; general formula; hydrazino
Prior art date: 1978-03-20

Application number

SE7902393A

Other languages

English (en)

Swedish (sv)

Other versions

SE7902393L (sv

Inventor

T Rettegi

E Mago

L Toldy

J Borsi

L Tardos

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.)

1978-03-20

Filing date

1979-03-16

Publication date

1985-06-03

1979-03-16 Application filed by Richter Gedeon Vegyeszet filed Critical Richter Gedeon Vegyeszet

1979-09-21 Publication of SE7902393L publication Critical patent/SE7902393L/xx

1985-06-03 Publication of SE439163B publication Critical patent/SE439163B/sv

Links

239000000825 pharmaceutical preparation Substances 0.000 title claims description 7
150000001875 compounds Chemical class 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
-1 N'-acetylhydrazino Chemical group 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 4
230000000694 effects Effects 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
230000000794 anti-serotonin Effects 0.000 claims description 2
239000003420 antiserotonin agent Substances 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims 1
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
239000007858 starting material Substances 0.000 description 13
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
239000000243 solution Substances 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
238000000034 method Methods 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
KPJZHOPZRAFDTN-ZRGWGRIASA-N (6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)CC)C2)=C3C2=CN(C)C3=C1 KPJZHOPZRAFDTN-ZRGWGRIASA-N 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
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 group 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 4
LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 4
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
239000000126 substance Substances 0.000 description 4
238000012360 testing method Methods 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
206010030113 Oedema Diseases 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
QWJJYAZVHWUTOB-PSOPSSQASA-N [(6ar,9r,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]methylhydrazine Chemical compound C1=CC([C@H]2C[C@@H](CNN)CN([C@@H]2C2)C)=C3C2=CNC3=C1 QWJJYAZVHWUTOB-PSOPSSQASA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
239000011976 maleic acid Substances 0.000 description 3
230000004048 modification Effects 0.000 description 3
238000012986 modification Methods 0.000 description 3
239000003921 oil Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 2
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 2
YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
241000208202 Linaceae Species 0.000 description 2
235000004431 Linum usitatissimum Nutrition 0.000 description 2
ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000499 gel Substances 0.000 description 2
150000002540 isothiocyanates Chemical class 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
229960001186 methysergide Drugs 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229940076279 serotonin Drugs 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
UNBRKDKAWYKMIV-QWQRMKEZSA-N (6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)CC)C2)=C3C2=CNC3=C1 UNBRKDKAWYKMIV-QWQRMKEZSA-N 0.000 description 1
GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
BHQJPULCUZTAHS-NYSBEXSLSA-N 1-[[(6ar,9r,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]methylamino]-3-phenylthiourea Chemical compound C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC=C(C=34)C2)C1)C)NNC(=S)NC1=CC=CC=C1 BHQJPULCUZTAHS-NYSBEXSLSA-N 0.000 description 1
JKAHWGPTNVUTNB-QOBVVAFRSA-N 2-[(6ar,10ar)-5-chloro-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]acetonitrile Chemical compound C1=CC([C@H]2CC(CC#N)CN([C@@H]2C2)C)=C3C2=C(Cl)NC3=C1 JKAHWGPTNVUTNB-QOBVVAFRSA-N 0.000 description 1
CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 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
241000700159 Rattus Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
NZHKBVYGAOGPCA-SGIREYDYSA-N [(6ar,9r,10ar)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-yl]methylhydrazine Chemical compound C1=CC([C@H]2C[C@@H](CNN)CN([C@@H]2C2)C)=C3C2=CN(C)C3=C1 NZHKBVYGAOGPCA-SGIREYDYSA-N 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
235000016720 allyl isothiocyanate Nutrition 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
239000003124 biologic agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
230000008602 contraction Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000010200 folin Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000011835 investigation Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
CXCUWGLJCPLHAN-FDQGKXFDSA-N n'-[[(6ar,9r,10ar)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-yl]methyl]acetohydrazide Chemical compound C1=CC([C@H]2C[C@@H](CNNC(C)=O)CN([C@@H]2C2)C)=C3C2=CN(C)C3=C1 CXCUWGLJCPLHAN-FDQGKXFDSA-N 0.000 description 1
SXSBORPBHTXDGA-XGWLTEMNSA-N n'-[[(6ar,9r,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]methyl]acetohydrazide Chemical compound C1=CC([C@H]2C[C@@H](CNNC(C)=O)CN([C@@H]2C2)C)=C3C2=CNC3=C1 SXSBORPBHTXDGA-XGWLTEMNSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000012071 phase Substances 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
229940121356 serotonin receptor antagonist Drugs 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
239000000080 wetting agent 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
- 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
- A61P25/24—Antidepressants
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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

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

SE7902393A 1978-03-20 1979-03-16 8beta-hydrozinometyl-ergolin-derivat och farmaceutisk beredning derav SE439163B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU78GO1394A HU178396B (en)	1978-03-20	1978-03-20	Process for producing new 8-beta-hydrazion-methyl-ergoline-and -ergolene derivatives

Publications (2)

Publication Number	Publication Date
SE7902393L SE7902393L (sv)	1979-09-21
SE439163B true SE439163B (sv)	1985-06-03

Family

ID=10996848

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE7902393A SE439163B (sv)	1978-03-20	1979-03-16	8beta-hydrozinometyl-ergolin-derivat och farmaceutisk beredning derav

Country Status (17)

Country	Link
US (1)	US4235912A (fr)
JP (1)	JPS54141800A (fr)
AU (1)	AU520004B2 (fr)
BE (1)	BE874932A (fr)
CA (1)	CA1120470A (fr)
CH (1)	CH640235A5 (fr)
DE (1)	DE2910734A1 (fr)
DK (1)	DK147301C (fr)
ES (1)	ES478812A1 (fr)
FR (1)	FR2422661A1 (fr)
GB (1)	GB2017096B (fr)
HU (1)	HU178396B (fr)
IL (1)	IL56817A (fr)
IT (1)	IT1166711B (fr)
NL (1)	NL7902148A (fr)
SE (1)	SE439163B (fr)
SU (1)	SU922108A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2112382B (en) *	1981-11-06	1985-03-06	Erba Farmitalia	Ergoline derivatives
HU190105B (en) *	1983-06-03	1986-08-28	Gyogyszerkutato Intezet	Process for production of pirazolyl-methyl-ergolin- derivatives and their acid additional salts

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU170271B (fr)	1974-07-19	1977-05-28

1978
- 1978-03-20 HU HU78GO1394A patent/HU178396B/hu not_active IP Right Cessation
1979
- 1979-03-07 IL IL56817A patent/IL56817A/xx unknown
- 1979-03-13 AU AU45025/79A patent/AU520004B2/en not_active Ceased
- 1979-03-16 SE SE7902393A patent/SE439163B/sv unknown
- 1979-03-19 FR FR7906831A patent/FR2422661A1/fr active Granted
- 1979-03-19 DE DE19792910734 patent/DE2910734A1/de not_active Withdrawn
- 1979-03-19 BE BE1/9318A patent/BE874932A/fr not_active IP Right Cessation
- 1979-03-19 IT IT21095/79A patent/IT1166711B/it active
- 1979-03-19 DK DK112579A patent/DK147301C/da not_active IP Right Cessation
- 1979-03-19 US US06/021,947 patent/US4235912A/en not_active Expired - Lifetime
- 1979-03-19 CH CH254779A patent/CH640235A5/de not_active IP Right Cessation
- 1979-03-19 NL NL7902148A patent/NL7902148A/xx not_active Application Discontinuation
- 1979-03-19 GB GB7909607A patent/GB2017096B/en not_active Expired
- 1979-03-20 JP JP3184179A patent/JPS54141800A/ja active Granted
- 1979-03-20 SU SU792742152A patent/SU922108A1/ru active
- 1979-03-20 ES ES478812A patent/ES478812A1/es not_active Expired
- 1979-03-20 CA CA000323804A patent/CA1120470A/fr not_active Expired

Also Published As

Publication number	Publication date
HU178396B (en)	1982-04-28
DK147301C (da)	1985-01-02
GB2017096A (en)	1979-10-03
AU4502579A (en)	1979-09-27
JPS54141800A (en)	1979-11-05
AU520004B2 (en)	1982-01-07
GB2017096B (en)	1982-09-02
BE874932A (fr)	1979-09-19
DK112579A (da)	1979-09-21
IL56817A (en)	1981-11-30
CA1120470A (fr)	1982-03-23
US4235912A (en)	1980-11-25
JPS575237B2 (fr)	1982-01-29
CH640235A5 (de)	1983-12-30
ES478812A1 (es)	1979-08-01
IL56817A0 (en)	1979-05-31
NL7902148A (nl)	1979-09-24
SE7902393L (sv)	1979-09-21
IT1166711B (it)	1987-05-06
DK147301B (da)	1984-06-12
FR2422661A1 (fr)	1979-11-09
SU922108A1 (ru)	1982-04-23
IT7921095A0 (it)	1979-03-19
DE2910734A1 (de)	1979-09-27
FR2422661B1 (fr)	1982-01-29

Publication	Publication Date	Title
US5344926A (en)	1994-09-06	Process for producing staurosporine derivatives
CA2021685A1 (fr)	1991-01-26	1h-indazole-3-carboxamides substitues
HU201329B (en)	1990-10-28	Process for production of substituated on nitrogen atom of methil-amin group of staurosporen derivatives and medical compositions containing them
SK145792A3 (en)	1995-04-12	Rapamycin derivatives and pharmaceutical agents containing them
JPH05163280A (ja)	1993-06-29	二環式ラパマイシン
HU198054B (en)	1989-07-28	Process for producing rapqmycin derivatives and pharmaceutical compositions comprising such compounds as active ingredient
US3714149A (en)	1973-01-30	Pyridobenzodiazepinones
CZ213693A3 (en)	1994-05-18	Diindolepyrrolbenzodiazocines, process of their preparation and use, and a pharmaceutical mixture based thereon
EP0333176A2 (fr)	1989-09-20	Dérivé de la benzoxazinorifamycine substitué, procédé de préparation et agent antibactérien le contenant
SE439163B (sv)	1985-06-03	8beta-hydrozinometyl-ergolin-derivat och farmaceutisk beredning derav
US3985752A (en)	1976-10-12	6-Methyl-8-(substituted) methylergolines
US4299836A (en)	1981-11-10	Novel ergol-8-ene and ergolin compounds and process for preparing same
KR880001284B1 (ko)	1988-07-18	아지노 리파마이신 화합물의 제조방법
JPS63303991A (ja)	1988-12-12	エピポドフイロトキシングルコシドの窒素含有誘導体
US3681355A (en)	1972-08-01	Ergonarcarnines
CS250248B2 (en)	1987-04-16	Method of imidazole's tricyclic derivatives production
US3944582A (en)	1976-03-16	Carbamates of ergolines
KR20000010893A (ko)	2000-02-25	마피아 포에티다(mappia foetida)에서 분리한캄토테신골격화합물 및 이들의 신규한 치료제 및 의약품기질로서의 용도
US4460599A (en)	1984-07-17	Mitomycin analogs
JPH0378873B2 (fr)	1991-12-17
CN117677615A (zh)	2024-03-08	一种螺环化合物的盐型、晶型及其制备方法
US3772299A (en)	1973-11-13	P'-alkoxy-ergotamines
US4057635A (en)	1977-11-08	Carbamates of ergolines and therapeutic compositions therewith
SE455097B (sv)	1988-06-20	Peptidergotalkaloider, forfarande for deras framstellning och farmaceutisk komposition
US4004009A (en)	1977-01-18	Antihypertensive aryl pyrazolo[4,3-c]pyridazinones