NL8600430A - Ergoline-derivaten en preparaten die ze bevatten. - Google Patents

Ergoline-derivaten en preparaten die ze bevatten. Download PDF

Info

Publication number: NL8600430A
Authority: NL; Netherlands
Prior art keywords: methyl; mixture; formula; added; methylergolinyl
Prior art date: 1985-02-21

Application number

NL8600430A

Other languages

English (en)

Dutch (nl)

Original Assignee

Maruko Pharmaceutical Co

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.)

1985-02-21

Filing date

1986-02-20

Publication date

1986-09-16

1985-12-28 Priority claimed from JP29920385A external-priority patent/JPH0699429B2/ja

1986-02-20 Application filed by Maruko Pharmaceutical Co filed Critical Maruko Pharmaceutical Co

1986-09-16 Publication of NL8600430A publication Critical patent/NL8600430A/nl

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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 title claims description 8
238000002360 preparation method Methods 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims description 48
230000000694 effects Effects 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 9
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 8
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
238000000034 method Methods 0.000 claims description 4
229960002317 succinimide Drugs 0.000 claims description 4
PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 claims description 3
ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 claims description 3
FUOZJYASZOSONT-UHFFFAOYSA-N 2-propan-2-yl-1h-imidazole Chemical compound CC(C)C1=NC=CN1 FUOZJYASZOSONT-UHFFFAOYSA-N 0.000 claims description 3
MKBBSFGKFMQPPC-UHFFFAOYSA-N 2-propyl-1h-imidazole Chemical compound CCCC1=NC=CN1 MKBBSFGKFMQPPC-UHFFFAOYSA-N 0.000 claims description 3
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 3
ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 claims description 3
VLDUBDZWWNLZCU-UHFFFAOYSA-N ethyl 5-methyl-1h-imidazole-4-carboxylate Chemical compound CCOC(=O)C=1NC=NC=1C VLDUBDZWWNLZCU-UHFFFAOYSA-N 0.000 claims description 3
150000003536 tetrazoles Chemical class 0.000 claims description 3
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 2
HCXJFMDOHDNDCC-UHFFFAOYSA-N 5-$l^{1}-oxidanyl-3,4-dihydropyrrol-2-one Chemical group O=C1CCC(=O)[N]1 HCXJFMDOHDNDCC-UHFFFAOYSA-N 0.000 claims description 2
239000013543 active substance Substances 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
125000003226 pyrazolyl group Chemical group 0.000 claims description 2
SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 claims 1
125000003831 tetrazolyl group Chemical group 0.000 claims 1
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 28
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
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239000000126 substance Substances 0.000 description 17
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CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 3
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UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
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CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
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208000036029 Uterine contractions during pregnancy Diseases 0.000 description 1
210000000683 abdominal cavity Anatomy 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
239000008272 agar Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
229940069428 antacid Drugs 0.000 description 1
239000003159 antacid agent Substances 0.000 description 1
230000001458 anti-acid effect Effects 0.000 description 1
239000003699 antiulcer agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
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239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
235000012216 bentonite Nutrition 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000002775 capsule Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
229960000541 cetyl alcohol Drugs 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
210000001653 corpus striatum Anatomy 0.000 description 1
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
230000000994 depressogenic effect Effects 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
229960003638 dopamine Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000001819 effect on gene Effects 0.000 description 1
229960004943 ergotamine Drugs 0.000 description 1
OFKDAAIKGIBASY-VFGNJEKYSA-N ergotamine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2C(C3=CC=CC4=NC=C([C]34)C2)=C1)C)C1=CC=CC=C1 OFKDAAIKGIBASY-VFGNJEKYSA-N 0.000 description 1
XCGSFFUVFURLIX-UHFFFAOYSA-N ergotaminine Natural products C1=C(C=2C=CC=C3NC=C(C=23)C2)C2N(C)CC1C(=O)NC(C(N12)=O)(C)OC1(O)C1CCCN1C(=O)C2CC1=CC=CC=C1 XCGSFFUVFURLIX-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
201000005917 gastric ulcer Diseases 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
210000004907 gland Anatomy 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
231100000086 high toxicity Toxicity 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate 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
229960003442 meclofenoxate Drugs 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
206010027599 migraine Diseases 0.000 description 1
230000004899 motility Effects 0.000 description 1
XVDBWWRIXBMVJV-UHFFFAOYSA-N n-[bis(dimethylamino)phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(N(C)C)N(C)C XVDBWWRIXBMVJV-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000002746 orthostatic effect Effects 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000006187 pill Substances 0.000 description 1
230000001817 pituitary effect Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
230000001012 protector Effects 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
210000001187 pylorus Anatomy 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
210000000813 small intestine Anatomy 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000035488 systolic blood pressure Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
210000000707 wrist Anatomy 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NL8600430A 1985-02-21 1986-02-20 Ergoline-derivaten en preparaten die ze bevatten. NL8600430A (nl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP3343085		1985-02-21
JP3343085		1985-02-21
JP29920385		1985-12-28
JP29920385A JPH0699429B2 (ja)	1985-02-21	1985-12-28	エルゴリン誘導体およびその酸付加塩

Publications (1)

Publication Number	Publication Date
NL8600430A true NL8600430A (nl)	1986-09-16

Family

ID=26372109

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8600430A NL8600430A (nl)	1985-02-21	1986-02-20	Ergoline-derivaten en preparaten die ze bevatten.

Country Status (13)

Country	Link
US (1)	US4713457A (it)
AU (1)	AU591094B2 (it)
BE (1)	BE904254A (it)
CA (1)	CA1292736C (it)
CH (1)	CH666270A5 (it)
DE (1)	DE3605676C2 (it)
ES (1)	ES8704502A1 (it)
FR (1)	FR2577553B1 (it)
GB (1)	GB2173189B (it)
HU (1)	HU195655B (it)
IT (1)	IT1203744B (it)
NL (1)	NL8600430A (it)
SE (1)	SE466016B (it)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8714767D0 (en) *	1987-06-24	1987-07-29	Erba Farmitalia	Egoline derivatives
GB8617907D0 (en) *	1986-07-22	1986-08-28	Erba Farmitalia	Tetracyclic indole derivatives
GB8702364D0 (en) *	1987-02-03	1987-03-11	Erba Farmitalia	Ergolinyl heterocycles
GB9006772D0 (en) *	1990-03-27	1990-05-23	Erba Carlo Spa	4-piperidinyl-ergoline derivatives

Family Cites Families (25)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH551976A (de) *	1971-05-19	1974-07-31	Sandoz Ag	Verfahren zur herstellung neuer 6-methyl-8(beta)-(ureidomethyl) ergolen-derivate.
CH551975A (de) *	1971-05-19	1974-07-31	Sandoz Ag	Verfahren zur herstellung neuer 6-methyl-8(beta)-(ureidomethyl) ergolen-derivate.
US4199579A (en) *	1975-03-14	1980-04-22	Siphar S. A.	Carbamates of 2-haloergolines and 2-haloergolenes and process for the preparation thereof
HU172649B (hu) *	1975-04-24	1978-11-28	Gyogyszerkutato Intezet	Sposob poluchenija novykh biologicheski aktivnykh lizergamidov
YU39278B (en) *	1976-12-22	1984-10-31	Lek Tovarna Farmacevtskih	Process for preparing 5-bromo nicotinic acid esters
DE2802023A1 (de) *	1977-01-28	1978-08-03	Sandoz Ag	Neue ergotderivate, ihre herstellung und verwendung
CH628049A5 (en) *	1977-03-25	1982-02-15	Sandoz Ag	Process for the preparation of ergolene derivatives
YU216177A (en) *	1977-09-09	1984-02-29	Rudolf Rucman	Process for preparing 2-bromo ergosine
US4166182A (en) *	1978-02-08	1979-08-28	Eli Lilly And Company	6-n-propyl-8-methoxymethyl or methylmercaptomethylergolines and related compounds
FR2421176A1 (fr) *	1978-03-29	1979-10-26	Sandoz Sa	Nouveaux derives de l'ergot de seigle, leur preparation et leur application comme medicaments
YU40046B (en) *	1978-09-04	1985-06-30	Lek Tovarna Farmacevtskih	Process for preparing 2-bromo-9,10-dihydroergosine
YU40533B (en) *	1978-09-04	1986-02-28	Lek Tovarna Farmacevtskih	Process for preparing 2-bromoergosinine
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
GB2056437A (en) *	1979-08-07	1981-03-18	Erba Farmitalia	Secoergoline derivatives
ZA812103B (en) *	1980-04-03	1982-04-28	Erba Farmitalia	Ergoline derivatives
NL189462C (nl) *	1980-04-03	1993-04-16	Erba Carlo Spa	Ergolinederivaten met antiprolactinische en/of antihypertensieve eigenschappen en farmaceutische preparaat daarvan.
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
CH645894A5 (en) *	1981-02-24	1984-10-31	Sandoz Ag	Ergoline derivatives, their preparation and use
GB2112382B (en) *	1981-11-06	1985-03-06	Erba Farmitalia	Ergoline derivatives
GB2120242A (en) *	1982-04-30	1983-11-30	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
DE3309493A1 (de) *	1983-03-14	1984-09-20	Schering AG, 1000 Berlin und 4709 Bergkamen	Neue ergolin-derivate, verfahren zu ihrer herstellung sowie verwendung als arzneimittel
PH21123A (en) *	1983-04-28	1987-07-27	Erba Farmitalia	Ergoline derivatives
GB8311679D0 (en) *	1983-04-28	1983-06-02	Erba Farmitalia	Ergoline derivatives

1986
- 1986-02-12 GB GB08603442A patent/GB2173189B/en not_active Expired
- 1986-02-13 AU AU53465/86A patent/AU591094B2/en not_active Ceased
- 1986-02-19 CA CA000502188A patent/CA1292736C/en not_active Expired - Lifetime
- 1986-02-20 SE SE8600786A patent/SE466016B/sv not_active IP Right Cessation
- 1986-02-20 HU HU86711A patent/HU195655B/hu not_active IP Right Cessation
- 1986-02-20 CH CH682/86A patent/CH666270A5/de not_active IP Right Cessation
- 1986-02-20 BE BE0/216288A patent/BE904254A/fr not_active IP Right Cessation
- 1986-02-20 IT IT47672/86A patent/IT1203744B/it active
- 1986-02-20 NL NL8600430A patent/NL8600430A/nl not_active Application Discontinuation
- 1986-02-21 ES ES552258A patent/ES8704502A1/es not_active Expired
- 1986-02-21 FR FR868602440A patent/FR2577553B1/fr not_active Expired - Lifetime
- 1986-02-21 US US06/831,676 patent/US4713457A/en not_active Expired - Fee Related
- 1986-02-21 DE DE3605676A patent/DE3605676C2/de not_active Expired - Fee Related

Also Published As

Publication number	Publication date
HUT40121A (en)	1986-11-28
IT1203744B (it)	1989-02-23
US4713457A (en)	1987-12-15
CA1292736C (en)	1991-12-03
GB8603442D0 (en)	1986-03-19
DE3605676A1 (de)	1986-09-18
GB2173189B (en)	1988-04-27
HU195655B (en)	1988-06-28
CH666270A5 (de)	1988-07-15
ES552258A0 (es)	1987-04-16
SE8600786D0 (sv)	1986-02-20
GB2173189A (en)	1986-10-08
SE8600786L (sv)	1986-08-22
FR2577553B1 (fr)	1991-06-21
DE3605676C2 (de)	1998-04-09
BE904254A (fr)	1986-06-16
AU591094B2 (en)	1989-11-30
SE466016B (sv)	1991-12-02
ES8704502A1 (es)	1987-04-16
AU5346586A (en)	1986-08-28
FR2577553A1 (fr)	1986-08-22
IT8647672A0 (it)	1986-02-20

Legal Events

Date	Code	Title
1993-04-01	BA	A request for search or an international-type search has been filed
1993-05-03	BB	A search report has been drawn up
1993-10-01	BC	A request for examination has been filed
1999-11-01	BV	The patent application has lapsed

Publication	Publication Date	Title
US5057614A (en)	1991-10-15	Substituted pyrroles
KR910006637B1 (ko)	1991-08-29	트립타민 유도체의 제조방법
NZ551812A (en)	2009-07-31	5-substituted-2-phenylamino-benzamide as MEK inhibitor
CA3110576A1 (en)	2020-03-26	Compounds for treating certain leukemias
JP2581556B2 (ja)	1997-02-12	新規なドパミンベ−タヒドロキシラ−ゼ抑制剤
US3734924A (en)	1973-05-22	Carboxamidines
IE57101B1 (en)	1992-04-22	Thiazolidine derivatives
CZ298805B6 (cs)	2008-02-06	Derivát arylalkanoylpyridazinu, zpusob jeho prípravy a farmaceutický prostredek, který ho obsahuje
IL101483A (en)	1995-12-08	Benzimidazole derivatives their preparation and pharmaceutical compositions containing them
AU715751B2 (en)	2000-02-10	New benzimidazole, benzoxazole and benzothiazole compounds, process for preparing them and pharmaceutical compositions containing them
EP0273401B1 (en)	1992-11-11	Isoindolin-1-one derivative and antiarrhythmic agent
EP0009655A1 (en)	1980-04-16	6-Amino substituted N-pyrrolyl-3-pyridazine amines, their preparation, and pharmaceutically antihypertensive compositions containing them
USRE36736E (en)	2000-06-13	Substituted pyrroles
JP2834506B2 (ja)	1998-12-09	新規チエニルオキシ‐アルキルアミン誘導体、その製法及びこの化合物を含有する医薬
CA1292736C (en)	1991-12-03	Ergoline derivatives and acid addition salts thereof
GB2093450A (en)	1982-09-02	2,1,3-benzothiadiazole derivatives
US4810800A (en)	1989-03-07	Novel imidazole dopamine beta hydroxylase inhibitors
MXPA02005866A (es)	2002-10-23	Derivados de heterociclo y drogas.
US3047571A (en)	1962-07-31	Derivatives of oxopiperidinyl phenthiazines
KR930003612B1 (ko)	1993-05-08	에르골린 유도체 및 그 산부가염의 제조방법
US5189052A (en)	1993-02-23	Thione dopamine beta hydroxylase inhibitors
US5057613A (en)	1991-10-15	Novel thione dopamine beta hydroxylase inhibitors
US3549756A (en)	1970-12-22	Antitrichomonal compositions containing 1-substituted - 2 - morpholinyl or thiamorpholinyl-5-nitroimidazoles
EP0102580B1 (en)	1986-04-09	Substituted 1,3,4-benzotriazepines, a method of preparing the same and theire use as medicaments
DK154218B (da)	1988-10-24	Pyrazolopyridinderivater eller farmaceutisk acceptable salte deraf samt farmaceutisk praeparat indeholdende en eller flere af disse forbindelser