NL8002811A - Secoergolineverbindingen. - Google Patents

Secoergolineverbindingen. Download PDF

Info

Publication number: NL8002811A
Authority: NL; Netherlands
Prior art keywords: secoergoline; dimethyl; methoxy; group; general formula
Prior art date: 1979-08-07

Application number

NL8002811A

Other languages

English (en)

Dutch (nl)

Original Assignee

Erba Farmitalia

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.)

1979-08-07

Filing date

1980-05-14

Publication date

1981-02-10

1980-05-14 Application filed by Erba Farmitalia filed Critical Erba Farmitalia

1981-02-10 Publication of NL8002811A publication Critical patent/NL8002811A/nl

Links

150000001875 compounds Chemical class 0.000 title claims description 46
-1 2-carbamoyl-2-cyanoethyl Chemical group 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
239000003054 catalyst Substances 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
125000004434 sulfur atom Chemical group 0.000 claims description 6
238000000034 method Methods 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
238000005984 hydrogenation reaction Methods 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
229910052763 palladium Inorganic materials 0.000 claims description 3
229910052697 platinum Inorganic materials 0.000 claims description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 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 description 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
101100260565 Dictyostelium discoideum thyA gene Proteins 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
101150068774 thyX gene Proteins 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000006260 foam Substances 0.000 description 9
238000001228 spectrum Methods 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
238000001704 evaporation Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000002904 solvent Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
XFVXVJZNBUKGMU-WBVHZDCISA-N [(6aR,10aS)-10a-methoxy-7-methyl-4,6,6a,8-tetrahydroindolo[4,3-fg]quinolin-9-yl]methanol Chemical compound CN1CC(=C[C@@]2(C=3C=CC=C4NC=C(C[C@@H]12)C34)OC)CO XFVXVJZNBUKGMU-WBVHZDCISA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000003480 eluent Substances 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 1
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
QCSOPPGLMUQBCN-CMCURQENSA-N 2-[(6aR,10aR)-7-methyl-6,6a,8,10a-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]-2-amino-N,N-dimethylacetamide Chemical compound CN1CC(=C[C@@H]2C=3C=CC=C4NC=C(C[C@@H]12)C34)C(N)C(N(C)C)=O QCSOPPGLMUQBCN-CMCURQENSA-N 0.000 description 1
KEFZOYQFQLHWPT-CMCURQENSA-N 2-[(6aR,10aR)-7-methyl-6,6a,8,10a-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]-2-amino-N,N-dimethylethanethioamide Chemical compound CN1CC(=C[C@@H]2C=3C=CC=C4NC=C(C[C@@H]12)C34)C(N)C(N(C)C)=S KEFZOYQFQLHWPT-CMCURQENSA-N 0.000 description 1
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 compound 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 1
101150065749 Churc1 gene Proteins 0.000 description 1
YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
102100038239 Protein Churchill Human genes 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
239000013543 active substance Substances 0.000 description 1
YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
239000002160 alpha blocker Substances 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
230000001263 anti-prolactin effect Effects 0.000 description 1
229940124575 antispasmodic agent Drugs 0.000 description 1
JXULCAZKLCIHTK-CKALXEAQSA-N benzyl 2-[(6aR,10aR)-7-methyl-6,6a,8,10a-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]-2-aminoacetate Chemical compound CN1CC(=C[C@@H]2C=3C=CC=C4NC=C(C[C@@H]12)C34)C(N)C(=O)OCC3=CC=CC=C3 JXULCAZKLCIHTK-CKALXEAQSA-N 0.000 description 1
LPPZBBGQRNLWAH-KYPFDINASA-N benzyl 2-[(6aR,10aS)-10a-methoxy-7-methyl-4,6,6a,8-tetrahydroindolo[4,3-fg]quinolin-9-yl]-2-aminoacetate Chemical compound C(C1=CC=CC=C1)OC(=O)C(C=1CN([C@@H]2CC3=CNC4=CC=CC([C@]2(C=1)OC)=C34)C)N LPPZBBGQRNLWAH-KYPFDINASA-N 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000812 cholinergic antagonist Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
CXDGRSYTPLHQMC-UHFFFAOYSA-N ethyl 2-cyanoacetate;sodium Chemical compound [Na].CCOC(=O)CC#N CXDGRSYTPLHQMC-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
208000021822 hypotensive Diseases 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
PMRYVIKBURPHAH-UHFFFAOYSA-N methimazole Chemical compound CN1C=CNC1=S PMRYVIKBURPHAH-UHFFFAOYSA-N 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension 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
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/90—Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles

Landscapes

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

NL8002811A 1979-08-07 1980-05-14 Secoergolineverbindingen. NL8002811A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB7927525		1979-08-07
GB7927525		1979-08-07

Publications (1)

Publication Number	Publication Date
NL8002811A true NL8002811A (nl)	1981-02-10

Family

ID=10507051

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8002811A NL8002811A (nl)	1979-08-07	1980-05-14	Secoergolineverbindingen.

Country Status (6)

Country	Link
JP (1)	JPS5626874A (it)
BE (1)	BE883294A (it)
DE (1)	DE3018477A1 (it)
FR (1)	FR2463128A1 (it)
IT (1)	IT1196914B (it)
NL (1)	NL8002811A (it)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2540625Y2 (ja) *	1991-04-10	1997-07-09	セイレイ工業株式会社	コンバイン

1980
- 1980-05-14 BE BE0/200610A patent/BE883294A/fr not_active IP Right Cessation
- 1980-05-14 NL NL8002811A patent/NL8002811A/nl not_active Application Discontinuation
- 1980-05-14 DE DE19803018477 patent/DE3018477A1/de not_active Withdrawn
- 1980-05-15 IT IT22082/80A patent/IT1196914B/it active
- 1980-05-15 JP JP6465980A patent/JPS5626874A/ja active Pending
- 1980-05-16 FR FR8011002A patent/FR2463128A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
IT8022082A0 (it)	1980-05-15
JPS5626874A (en)	1981-03-16
IT1196914B (it)	1988-11-25
DE3018477A1 (de)	1981-02-26
FR2463128A1 (fr)	1981-02-20
BE883294A (fr)	1980-09-01

Legal Events

Date	Code	Title	Description
1983-01-03	BV	The patent application has lapsed

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FI94959C (fi)	1995-11-27	Menetelmä valmistaa 2,3,4,5-tetrahydro-5-metyyli-1-/(5-metyyli-1H-imidatsol-4-yyli)-metyyli)/-1H-pyrido/4,3-b/-indol-1-onia