CA1156648A - Process for preparing ergoline derivatives - Google Patents

Process for preparing ergoline derivatives

Info

Publication number: CA1156648A
Authority: CA; Canada
Prior art keywords: beta; carbonyl; urea; ergoline; carboxy
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

CA000374134A

Other languages

English (en)

French (fr)

Inventor

Patricia Salvati

Enrico Di Salle

Germano Bosisio

Anna M. Caravaggi

Aldemio Temperilli

Osvaldo Sapini

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.)

Pfizer Italia SRL

Original Assignee

Farmitalia Carlo Erba SRL

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

1981-03-30

Publication date

1983-11-08

1981-03-30 Application filed by Farmitalia Carlo Erba SRL filed Critical Farmitalia Carlo Erba SRL

1983-11-08 Application granted granted Critical

1983-11-08 Publication of CA1156648A publication Critical patent/CA1156648A/en

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims 2
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 abstract description 12
238000006243 chemical reaction Methods 0.000 claims abstract description 5
239000004202 carbamide Substances 0.000 claims description 90
238000000034 method Methods 0.000 claims description 62
150000001875 compounds Chemical class 0.000 claims description 56
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 17
BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 claims description 16
BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 claims description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
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
150000007522 mineralic acids Chemical class 0.000 claims description 6
IDVWLLCLTVBSCS-UHFFFAOYSA-N n,n'-ditert-butylmethanediimine Chemical compound CC(C)(C)N=C=NC(C)(C)C IDVWLLCLTVBSCS-UHFFFAOYSA-N 0.000 claims description 6
150000007524 organic acids Chemical class 0.000 claims description 6
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 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
NASVTBDJHWPMOO-UHFFFAOYSA-N n,n'-dimethylmethanediimine Chemical compound CN=C=NC NASVTBDJHWPMOO-UHFFFAOYSA-N 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
239000000126 substance Substances 0.000 claims 26
239000000010 aprotic solvent Substances 0.000 claims 4
230000005494 condensation Effects 0.000 claims 2
238000009833 condensation Methods 0.000 claims 2
150000007530 organic bases Chemical class 0.000 claims 2
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 16
230000001077 hypotensive effect Effects 0.000 abstract description 10
150000001718 carbodiimides Chemical class 0.000 abstract description 3
208000001953 Hypotension Diseases 0.000 abstract description 2
208000021822 hypotensive Diseases 0.000 abstract description 2
RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 20
241000700159 Rattus Species 0.000 description 10
229960002474 hydralazine Drugs 0.000 description 10
238000011282 treatment Methods 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
231100000419 toxicity Toxicity 0.000 description 6
230000001988 toxicity Effects 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
102000003946 Prolactin Human genes 0.000 description 4
108010057464 Prolactin Proteins 0.000 description 4
229940083181 centrally acting adntiadrenergic agent methyldopa Drugs 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000003814 drug Substances 0.000 description 4
230000000095 emetic effect Effects 0.000 description 4
238000011156 evaluation Methods 0.000 description 4
229940097325 prolactin Drugs 0.000 description 4
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 3
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
230000036772 blood pressure Effects 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
231100000673 dose–response relationship Toxicity 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
150000007513 acids Chemical class 0.000 description 2
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 2
230000001263 anti-prolactin effect Effects 0.000 description 2
230000036471 bradycardia Effects 0.000 description 2
208000006218 bradycardia Diseases 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
229940125904 compound 1 Drugs 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical class OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
LPMDNOPQLGRDMA-UHFFFAOYSA-N n'-butylmethanediimine Chemical compound CCCCN=C=N LPMDNOPQLGRDMA-UHFFFAOYSA-N 0.000 description 2
230000035935 pregnancy Effects 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
238000005303 weighing Methods 0.000 description 2
WZDBQAUNHHSVCK-PXFYRTPJSA-N (6ar,10ar)-9-propyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline Chemical compound C1=CC([C@@H]2[C@H](NCC(C2)CCC)C2)=C3C2=CNC3=C1 WZDBQAUNHHSVCK-PXFYRTPJSA-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
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
125000006519 CCH3 Chemical group 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
206010017600 Galactorrhoea Diseases 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 1
241000577218 Phenes Species 0.000 description 1
208000032749 Pregnancy Diseases 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
229950001817 alpha-ergocryptine Drugs 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
229940030600 antihypertensive agent Drugs 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
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 1
229960002802 bromocriptine Drugs 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000002596 correlated effect Effects 0.000 description 1
230000000875 corresponding effect Effects 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
230000001419 dependent effect Effects 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000001647 drug administration Methods 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
125000001153 fluoro group Chemical group F* 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
238000003304 gavage Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
208000031424 hyperprolactinemia Diseases 0.000 description 1
230000001631 hypertensive 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
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
230000006651 lactation Effects 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
-1 n-propyl isopropyl Chemical group 0.000 description 1
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
230000028327 secretion Effects 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
239000000377 silicon dioxide Substances 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
238000011699 spontaneously hypertensive rat Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
QGVNJRROSLYGKF-UHFFFAOYSA-N thiobarbital Chemical compound CCC1(CC)C(=O)NC(=S)NC1=O QGVNJRROSLYGKF-UHFFFAOYSA-N 0.000 description 1
229940086542 triethylamine Drugs 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000374134A 1980-04-03 1981-03-30 Process for preparing ergoline derivatives Expired CA1156648A (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB8011234		1980-04-03
GB8011234		1980-04-03
GB8040575		1980-12-18
GB8040575		1980-12-18

Publications (1)

Publication Number	Publication Date
CA1156648A true CA1156648A (en)	1983-11-08

Family

ID=26275073

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000374134A Expired CA1156648A (en)	1980-04-03	1981-03-30	Process for preparing ergoline derivatives

Country Status (20)

Country	Link
AT (1)	AT375076B (fi)
AU (1)	AU540621B2 (fi)
CA (1)	CA1156648A (fi)
CH (1)	CH645896A5 (fi)
CS (1)	CS415291A3 (fi)
DE (1)	DE3112861A1 (fi)
DK (1)	DK148686C (fi)
ES (1)	ES8202003A1 (fi)
FI (1)	FI70412C (fi)
FR (1)	FR2479829B1 (fi)
GR (1)	GR74806B (fi)
HK (1)	HK67287A (fi)
IE (1)	IE51130B1 (fi)
IL (1)	IL62519A (fi)
IT (2)	IT1210473B (fi)
NL (3)	NL189462C (fi)
NZ (1)	NZ196670A (fi)
PT (1)	PT72785B (fi)
SE (1)	SE442637B (fi)
YU (1)	YU43011B (fi)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7939665B2 (en)	2007-05-04	2011-05-10	Apotex Pharmachem Inc.	Efficient process for the preparation of cabergoline and its intermediates

Families Citing this family (5)

* 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
GB0409785D0 (en)	2004-04-30	2004-06-09	Resolution Chemicals Ltd	Preparation of cabergoline
GB0505965D0 (en)	2005-03-23	2005-04-27	Resolution Chemicals Ltd	Preparation of cabergoline
US7339060B2 (en)	2005-03-23	2008-03-04	Resolution Chemicals, Ltd.	Preparation of cabergoline
EP2067780A1 (en) *	2007-12-07	2009-06-10	Axxonis Pharma AG	Ergoline derivatives as selective radical scavengers for neurons

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE396753B (sv) *	1970-05-18	1977-10-03	Richter Gedeon Vegyeszet	Analogiforfarande for framstellning av en forening tillhorande dihydrolysergsyraserien

1981
- 1981-03-26 NL NLAANVRAGE8101509,A patent/NL189462C/xx not_active IP Right Cessation
- 1981-03-30 NZ NZ196670A patent/NZ196670A/xx unknown
- 1981-03-30 IL IL62519A patent/IL62519A/xx not_active IP Right Cessation
- 1981-03-30 AT AT0148481A patent/AT375076B/de not_active IP Right Cessation
- 1981-03-30 CH CH214481A patent/CH645896A5/de not_active IP Right Cessation
- 1981-03-30 CA CA000374134A patent/CA1156648A/en not_active Expired
- 1981-03-31 AU AU68937/81A patent/AU540621B2/en not_active Expired
- 1981-03-31 DE DE19813112861 patent/DE3112861A1/de active Granted
- 1981-03-31 ES ES500911A patent/ES8202003A1/es not_active Expired
- 1981-03-31 FR FR8106422A patent/FR2479829B1/fr not_active Expired
- 1981-03-31 YU YU851/81A patent/YU43011B/xx unknown
- 1981-04-01 PT PT72785A patent/PT72785B/pt unknown
- 1981-04-01 IT IT8120866A patent/IT1210473B/it active
- 1981-04-01 GR GR64542A patent/GR74806B/el unknown
- 1981-04-01 IT IT20865/81A patent/IT1205241B/it active Protection Beyond IP Right Term
- 1981-04-01 IE IE754/81A patent/IE51130B1/en not_active IP Right Cessation
- 1981-04-02 FI FI811025A patent/FI70412C/fi not_active IP Right Cessation
- 1981-04-02 SE SE8102131A patent/SE442637B/sv not_active IP Right Cessation
- 1981-04-02 DK DK150781A patent/DK148686C/da not_active IP Right Cessation
1987
- 1987-09-17 HK HK672/87A patent/HK67287A/xx not_active IP Right Cessation
1991
- 1991-12-30 CS CS914152A patent/CS415291A3/cs unknown
1993
- 1993-06-24 NL NL930092C patent/NL930092I1/nl unknown
- 1993-06-24 NL NL930091C patent/NL930091I2/nl unknown

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7939665B2 (en)	2007-05-04	2011-05-10	Apotex Pharmachem Inc.	Efficient process for the preparation of cabergoline and its intermediates

Also Published As

Publication number	Publication date
NL930092I1 (nl)	1993-10-01
NL930091I1 (nl)	1993-10-01
FI70412B (fi)	1986-03-27
SE8102131L (sv)	1981-10-04
NL930091I2 (nl)	1995-01-02
ATA148481A (de)	1983-11-15
DE3112861C2 (fi)	1989-06-01
ES500911A0 (es)	1982-01-16
NL189462C (nl)	1993-04-16
NL189462B (nl)	1992-11-16
CH645896A5 (de)	1984-10-31
NL8101509A (nl)	1981-11-02
DK150781A (da)	1981-10-04
DK148686C (da)	1986-03-10
DK148686B (da)	1985-09-02
IT8120865A0 (it)	1981-04-01
DE3112861A1 (de)	1982-01-07
IT8120866A0 (it)	1981-04-01
AU540621B2 (en)	1984-11-29
IT1205241B (it)	1989-03-15
HK67287A (en)	1987-09-25
IT1210473B (it)	1989-09-14
IE810754L (en)	1981-10-03
IL62519A0 (en)	1981-05-20
IE51130B1 (en)	1986-10-15
YU85181A (en)	1984-02-29
GR74806B (fi)	1984-07-12
ES8202003A1 (es)	1982-01-16
FI70412C (fi)	1986-09-19
YU43011B (en)	1989-02-28
FR2479829B1 (fr)	1987-07-24
FI811025L (fi)	1981-10-04
PT72785A (en)	1981-05-01
FR2479829A1 (fr)	1981-10-09
IL62519A (en)	1984-01-31
PT72785B (en)	1982-07-26
SE442637B (sv)	1986-01-20
AT375076B (de)	1984-06-25
AU6893781A (en)	1981-10-08
CS415291A3 (en)	1992-06-17
NZ196670A (en)	1982-12-07

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
CA1156648A (en)	1983-11-08	Process for preparing ergoline derivatives
US4022784A (en)	1977-05-10	5-[1-Hydroxy-2-(substituted-amino)]alkyl-8-substituted-carbostyril and -3,4-dihydrocarbostyril derivatives
PL114723B1 (en)	1981-02-28	Proces for preparing novel derivatives of morphine
JPS6210519B2 (fi)	1987-03-06
CA1252086A (en)	1989-04-04	Pyrazole derivatives with an ergoline skeleton, their acid addition salts, and a process for the preparation thereof
EP0008802B1 (en)	1982-07-21	Ergoline derivatives, their preparation and therapeutic composition containing them
GB2074566A (en)	1981-11-04	Ergoline Derivatives
US4310532A (en)	1982-01-12	Methods and piperidinyl-alkyl-benzamide composition for inhibiting H2 histamine receptors
US4496573A (en)	1985-01-29	1-Pyridylmethyl-3-acyl guanidines
KR950014866B1 (ko)	1995-12-16	에르골리닐 헤테로사이클
CA2109723C (en)	1999-07-20	Benzothiadiazine derivative
EP0091652B1 (en)	1986-02-26	Ergoline derivatives, process for producing the ergoline derivatives and pharmaceutical compositions containing them
US3957785A (en)	1976-05-18	Bβ-Pyrimidino-aminomethyl-10α-ergoline and 10α-methoxyergoline derivatives
HU183382B (en)	1984-04-28	Process for preparing ergoline derivatives and pharmaceutical compositions containing thereof as active substances
NO872094L (no)	1987-11-24	Fremgangsmaate for fremstilling av dbh-inhiberende forbindelser.
EP0394484A1 (en)	1990-10-31	Benzothiadiazepine derivatives
EP0964861B1 (en)	2005-04-27	Process for the production of tetrazolylbenzopyrans
GB2055370A (en)	1981-03-04	Ergol-8-ene and ergoline derivatives
KR840001473B1 (ko)	1984-09-28	에르골린 유도체의 제조방법
CA1278572C (en)	1991-01-02	Ameliorant of cerebral circulation and metabolism
US4591597A (en)	1986-05-27	Antidiabetic iminosulphonamides
CA1208630A (en)	1986-07-29	Ergot derivatives
US3927096A (en)	1975-12-16	Substituted benzylideneamino guanidines

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Date	Code	Title	Description
2000-11-08	MKEX	Expiry

CA1156648A - Process for preparing ergoline derivatives - Google Patents

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