NO128533B - - Google Patents
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- Publication number
- NO128533B NO128533B NO04110/71*[A NO411071A NO128533B NO 128533 B NO128533 B NO 128533B NO 411071 A NO411071 A NO 411071A NO 128533 B NO128533 B NO 128533B
- Authority
- NO
- Norway
- Prior art keywords
- didehydro
- methyl
- group
- formula
- methoxy
- Prior art date
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- -1 methoxy, amino Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 15
- 239000000155 melt Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229960004704 dihydroergotamine Drugs 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 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 2
- 229960004943 ergotamine Drugs 0.000 description 2
- 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 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- CYMKJNYIRLZRKM-XHDPSFHLSA-N (6aR,9S)-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide Chemical compound CN1C=C2C[C@H]3N(C[C@@H](C(N)=O)C=C3C=3C=CC=C1C32)C CYMKJNYIRLZRKM-XHDPSFHLSA-N 0.000 description 1
- GENAHGKEFJLNJB-IINYFYTJSA-N (6ar,9s)-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-carboxamide Chemical compound C1=CC(C2=C[C@@H](CN([C@@H]2C2)C)C(N)=O)=C3C2=CNC3=C1 GENAHGKEFJLNJB-IINYFYTJSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- KTOQRRDVVIDEAA-UHFFFAOYSA-N 2-methylpropane Chemical compound [CH2]C(C)C KTOQRRDVVIDEAA-UHFFFAOYSA-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 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 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- ZAGRKAFMISFKIO-UHFFFAOYSA-N Isolysergic acid Natural products C1=CC(C2=CC(CN(C2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-UHFFFAOYSA-N 0.000 description 1
- GENAHGKEFJLNJB-UHFFFAOYSA-N Lysergsaeure-amid Natural products C1=CC(C2=CC(CN(C2C2)C)C(N)=O)=C3C2=CNC3=C1 GENAHGKEFJLNJB-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000002908 adrenolytic effect Effects 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000003420 antiserotonin agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- ZAGRKAFMISFKIO-QMTHXVAHSA-N lysergic acid Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-QMTHXVAHSA-N 0.000 description 1
- SZUQJDJBJHBVBO-CTTKVJGISA-N metergotamine 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(C=3C=CC=C4N(C)C=C(C=34)C2)=C1)C)C1=CC=CC=C1 SZUQJDJBJHBVBO-CTTKVJGISA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- RNHDWLRHUJZABX-IAQYHMDHSA-N methyl (6ar,9r)-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-carboxylate Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)OC)C2)=C3C2=CNC3=C1 RNHDWLRHUJZABX-IAQYHMDHSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral 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
- 150000003254 radicals Chemical class 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
- 239000012453 solvate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000002560 therapeutic procedure 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
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/02—Ergot alkaloids of the cyclic peptide type
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT5466070 | 1970-11-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO128533B true NO128533B (de) | 1973-12-03 |
Family
ID=11287460
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO04110/71*[A NO128533B (de) | 1970-11-12 | 1971-11-08 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US3814765A (de) |
| JP (1) | JPS5344478B1 (de) |
| AT (1) | AT310953B (de) |
| AU (1) | AU466630B2 (de) |
| BE (1) | BE775145A (de) |
| CA (1) | CA926864A (de) |
| CH (1) | CH561721A5 (de) |
| CS (1) | CS165363B2 (de) |
| DE (1) | DE2155578C3 (de) |
| DK (1) | DK140842B (de) |
| FR (1) | FR2114476A5 (de) |
| GB (1) | GB1315439A (de) |
| HU (1) | HU164041B (de) |
| IE (1) | IE35794B1 (de) |
| IL (1) | IL38096A (de) |
| NL (1) | NL155016B (de) |
| NO (1) | NO128533B (de) |
| SE (1) | SE385707B (de) |
| SU (1) | SU406355A3 (de) |
| ZA (1) | ZA717541B (de) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4001242A (en) * | 1974-08-02 | 1977-01-04 | Eli Lilly And Company | D-6-methyl-8-formyl-10α-alkoxy-8-ergolene |
| US3929796A (en) * | 1974-08-02 | 1975-12-30 | Lilly Co Eli | Synthesis of penniclavine and elymoclavine |
| US3923812A (en) * | 1974-08-02 | 1975-12-02 | Lilly Co Eli | Synthesis of elymoclavine |
| US4054567A (en) * | 1975-08-11 | 1977-10-18 | Eli Lilly And Company | 6-Methyl-8β-hydroxymethyl-8-γ-substituted-9-ergolene compounds |
| US4082753A (en) * | 1976-02-17 | 1978-04-04 | Eli Lilly And Company | Penniclavine acetonide |
| SG181896A1 (en) * | 2009-12-23 | 2012-07-30 | Map Pharmaceuticals Inc | Novel ergoline analogs |
| CA2838991A1 (en) | 2011-06-23 | 2012-12-27 | Map Pharmaceuticals, Inc. | Novel fluoroergoline analogs |
| CA2859173A1 (en) | 2011-12-19 | 2013-06-27 | Map Pharmaceuticals, Inc. | Novel iso-ergoline derivatives |
| SG10201506202RA (en) | 2011-12-21 | 2015-09-29 | Map Pharmaceuticals Inc | Novel neuromodulatory compounds |
| US9012640B2 (en) | 2012-06-22 | 2015-04-21 | Map Pharmaceuticals, Inc. | Cabergoline derivatives |
-
1971
- 1971-10-04 US US00186385A patent/US3814765A/en not_active Expired - Lifetime
- 1971-11-01 NL NL717115017A patent/NL155016B/xx unknown
- 1971-11-01 AU AU35198/71A patent/AU466630B2/en not_active Expired
- 1971-11-08 NO NO04110/71*[A patent/NO128533B/no unknown
- 1971-11-08 FR FR7139938A patent/FR2114476A5/fr not_active Expired
- 1971-11-08 CS CS7815A patent/CS165363B2/cs unknown
- 1971-11-08 IE IE1406/71A patent/IE35794B1/xx unknown
- 1971-11-08 CA CA127063A patent/CA926864A/en not_active Expired
- 1971-11-08 IL IL38096A patent/IL38096A/en unknown
- 1971-11-08 GB GB5177271A patent/GB1315439A/en not_active Expired
- 1971-11-09 ZA ZA717541A patent/ZA717541B/xx unknown
- 1971-11-09 SE SE7114282A patent/SE385707B/xx unknown
- 1971-11-09 DK DK547271AA patent/DK140842B/da unknown
- 1971-11-09 SU SU1711760A patent/SU406355A3/ru active
- 1971-11-09 DE DE2155578A patent/DE2155578C3/de not_active Expired
- 1971-11-09 JP JP8876871A patent/JPS5344478B1/ja active Pending
- 1971-11-10 AT AT971071A patent/AT310953B/de not_active IP Right Cessation
- 1971-11-10 BE BE775145A patent/BE775145A/xx unknown
- 1971-11-11 CH CH1641871A patent/CH561721A5/xx not_active IP Right Cessation
- 1971-11-11 HU HUFA898A patent/HU164041B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU466630B2 (en) | 1975-11-06 |
| DE2155578C3 (de) | 1979-01-04 |
| FR2114476A5 (de) | 1972-06-30 |
| JPS5344478B1 (de) | 1978-11-29 |
| DK140842C (de) | 1980-05-05 |
| US3814765A (en) | 1974-06-04 |
| CS165363B2 (de) | 1975-12-22 |
| BE775145A (fr) | 1972-05-10 |
| ZA717541B (en) | 1972-08-30 |
| IE35794B1 (en) | 1976-05-26 |
| NL155016B (nl) | 1977-11-15 |
| AU3519871A (en) | 1973-05-10 |
| AT310953B (de) | 1973-10-25 |
| CA926864A (en) | 1973-05-22 |
| DE2155578B2 (de) | 1978-05-03 |
| SU406355A3 (de) | 1973-11-05 |
| NL7115017A (de) | 1972-05-16 |
| CH561721A5 (de) | 1975-05-15 |
| IL38096A0 (en) | 1972-01-27 |
| DK140842B (da) | 1979-11-26 |
| SE385707B (sv) | 1976-07-19 |
| DE2155578A1 (de) | 1972-05-18 |
| IE35794L (en) | 1972-05-12 |
| IL38096A (en) | 1976-02-29 |
| GB1315439A (en) | 1973-05-02 |
| HU164041B (de) | 1973-12-28 |
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