IE41564B1 - Ergot peptide alkaloids - Google Patents
Ergot peptide alkaloidsInfo
- Publication number
- IE41564B1 IE41564B1 IE1375/75A IE137575A IE41564B1 IE 41564 B1 IE41564 B1 IE 41564B1 IE 1375/75 A IE1375/75 A IE 1375/75A IE 137575 A IE137575 A IE 137575A IE 41564 B1 IE41564 B1 IE 41564B1
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- acid
- compound
- isopropyl
- acid addition
- Prior art date
Links
- 229930015720 peptide alkaloid Natural products 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 239000002253 acid Substances 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000008024 pharmaceutical diluent Substances 0.000 claims description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 4
- ORIBUSCBDFDAIQ-GYYYEOQOSA-N methyl (6ar,9r)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate Chemical compound C1=CC(C2[C@H](NC[C@@H](C2)C(=O)OC)C2)=C3C2=CNC3=C1 ORIBUSCBDFDAIQ-GYYYEOQOSA-N 0.000 abstract description 3
- 238000007127 saponification reaction Methods 0.000 abstract description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 1
- 238000007126 N-alkylation reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003791 organic solvent mixture Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 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
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000012320 chlorinating reagent Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000005526 vasoconstrictor agent Substances 0.000 description 2
- BXYYZJJBMGGKPU-WEWKJXCBSA-N (1S,2S,4R,7S)-4-amino-2-hydroxy-4-methyl-7-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecane-5,8-dione hydrochloride Chemical compound Cl.O=C1[C@H](C(C)C)N2C(=O)[C@](C)(N)O[C@@]2(O)[C@@H]2CCCN21 BXYYZJJBMGGKPU-WEWKJXCBSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- NBAGYSPOFSJXNM-IAQYHMDHSA-N lysergic acid methyl ester Chemical compound C1=CC=C2C3=C[C@@H](C(=O)OC)CN(C)[C@@H]3CC3=CN=C1[C]32 NBAGYSPOFSJXNM-IAQYHMDHSA-N 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000004307 sodium orthophenyl phenol Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH853374A CH602767A5 (US07223432-20070529-C00017.png) | 1974-06-21 | 1974-06-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE41564L IE41564L (en) | 1975-12-21 |
| IE41564B1 true IE41564B1 (en) | 1980-01-30 |
Family
ID=4341635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1375/75A IE41564B1 (en) | 1974-06-21 | 1975-06-19 | Ergot peptide alkaloids |
Country Status (21)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH601321A5 (US07223432-20070529-C00017.png) * | 1975-01-06 | 1978-07-14 | Sandoz Ag | |
| CH619468A5 (US07223432-20070529-C00017.png) * | 1976-01-12 | 1980-09-30 | Sandoz Ag | |
| 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 |
-
1975
- 1975-06-11 DE DE19752525962 patent/DE2525962A1/de not_active Withdrawn
- 1975-06-12 SE SE7506758A patent/SE7506758L/xx unknown
- 1975-06-12 DK DK266475AA patent/DK140670B/da unknown
- 1975-06-12 FI FI751753A patent/FI751753A/fi unknown
- 1975-06-13 NO NO752109A patent/NO752109L/no unknown
- 1975-06-16 GB GB25527/75A patent/GB1499420A/en not_active Expired
- 1975-06-17 NL NL7507177A patent/NL7507177A/xx not_active Application Discontinuation
- 1975-06-17 PH PH17276A patent/PH13361A/en unknown
- 1975-06-17 FR FR7518879A patent/FR2275212A1/fr active Granted
- 1975-06-19 DD DD186767A patent/DD118088A5/xx unknown
- 1975-06-19 AU AU82273/75A patent/AU503060B2/en not_active Expired
- 1975-06-19 ES ES438704A patent/ES438704A1/es not_active Expired
- 1975-06-19 HU HUSA2806A patent/HU169390B/hu unknown
- 1975-06-19 BE BE157509A patent/BE830441A/xx unknown
- 1975-06-19 IL IL47522A patent/IL47522A/en unknown
- 1975-06-19 IE IE1375/75A patent/IE41564B1/en unknown
- 1975-06-19 YU YU01573/75A patent/YU157375A/xx unknown
- 1975-06-20 AT AT473575A patent/AT356292B/de not_active IP Right Cessation
- 1975-06-20 JP JP50074583A patent/JPS5113798A/ja active Pending
- 1975-06-20 CA CA229,783A patent/CA1057285A/en not_active Expired
- 1975-06-20 ZA ZA3967A patent/ZA753967B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK140670C (US07223432-20070529-C00017.png) | 1980-03-17 |
| AT356292B (de) | 1980-04-25 |
| FR2275212B1 (US07223432-20070529-C00017.png) | 1979-08-10 |
| NL7507177A (nl) | 1975-12-23 |
| DK140670B (da) | 1979-10-22 |
| ES438704A1 (es) | 1977-06-01 |
| IE41564L (en) | 1975-12-21 |
| GB1499420A (en) | 1978-02-01 |
| AU8227375A (en) | 1976-12-23 |
| SE7506758L (sv) | 1975-12-22 |
| JPS5113798A (US07223432-20070529-C00017.png) | 1976-02-03 |
| IL47522A0 (en) | 1975-08-31 |
| AU503060B2 (en) | 1979-08-23 |
| HU169390B (US07223432-20070529-C00017.png) | 1976-11-28 |
| FR2275212A1 (fr) | 1976-01-16 |
| ZA753967B (en) | 1977-01-26 |
| NO752109L (US07223432-20070529-C00017.png) | 1975-12-23 |
| DK266475A (US07223432-20070529-C00017.png) | 1975-12-22 |
| CA1057285A (en) | 1979-06-26 |
| PH13361A (en) | 1980-03-20 |
| IL47522A (en) | 1977-12-30 |
| FI751753A (US07223432-20070529-C00017.png) | 1975-12-22 |
| DE2525962A1 (de) | 1976-01-08 |
| DD118088A5 (US07223432-20070529-C00017.png) | 1976-02-12 |
| ATA473575A (de) | 1979-09-15 |
| YU157375A (en) | 1982-05-31 |
| BE830441A (fr) | 1975-12-19 |
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