CS215105B2 - Method of making the 2-brom-alpha-ergocryptin - Google Patents
Method of making the 2-brom-alpha-ergocryptin Download PDFInfo
- Publication number
- CS215105B2 CS215105B2 CS778043A CS804377A CS215105B2 CS 215105 B2 CS215105 B2 CS 215105B2 CS 778043 A CS778043 A CS 778043A CS 804377 A CS804377 A CS 804377A CS 215105 B2 CS215105 B2 CS 215105B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- ergocryptine
- bromo
- alpha
- mmol
- ergocryptin
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- YDOTUXAWKBPQJW-UHFFFAOYSA-N alpha-Ergocryptinine Natural products C1=CC(C=2C(N(C)CC(C=2)C(=O)NC2(C(=O)N3C(C(N4CCCC4C3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=CNC3=C1 YDOTUXAWKBPQJW-UHFFFAOYSA-N 0.000 claims description 12
- 229950001817 alpha-ergocryptine Drugs 0.000 claims description 12
- YDOTUXAWKBPQJW-NSLWYYNWSA-N alpha-ergocryptine 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=CNC3=C1 YDOTUXAWKBPQJW-NSLWYYNWSA-N 0.000 claims description 12
- 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 claims description 10
- 238000000034 method Methods 0.000 claims description 7
- 239000003999 initiator Substances 0.000 claims description 6
- 150000004292 cyclic ethers Chemical class 0.000 claims description 5
- 239000012298 atmosphere Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 4
- QRADPXNAURXMSB-UHFFFAOYSA-N 2-bromo-1,1-dioxo-1,2-benzothiazol-3-one Chemical compound C1=CC=C2S(=O)(=O)N(Br)C(=O)C2=C1 QRADPXNAURXMSB-UHFFFAOYSA-N 0.000 claims description 3
- 230000031709 bromination Effects 0.000 claims description 3
- 238000005893 bromination reaction Methods 0.000 claims description 3
- 125000000532 dioxanyl group Chemical group 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- 102100024819 Prolactin Human genes 0.000 description 2
- 108010057464 Prolactin Proteins 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229940097325 prolactin Drugs 0.000 description 2
- GJNCXCPHNRATIQ-UHFFFAOYSA-N 1-bromoazepan-2-one Chemical compound BrN1CCCCCC1=O GJNCXCPHNRATIQ-UHFFFAOYSA-N 0.000 description 1
- MARXMDRWROUXMD-UHFFFAOYSA-N 2-bromoisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(Br)C(=O)C2=C1 MARXMDRWROUXMD-UHFFFAOYSA-N 0.000 description 1
- 206010000599 Acromegaly Diseases 0.000 description 1
- 201000000736 Amenorrhea Diseases 0.000 description 1
- 206010001928 Amenorrhoea Diseases 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 102000015554 Dopamine receptor Human genes 0.000 description 1
- 108050004812 Dopamine receptor Proteins 0.000 description 1
- 208000001287 Galactorrhea Diseases 0.000 description 1
- 206010017600 Galactorrhoea Diseases 0.000 description 1
- 108010051696 Growth Hormone Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 229940123796 Prolactin inhibitor Drugs 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 102100038803 Somatotropin Human genes 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 231100000540 amenorrhea Toxicity 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 229960004943 ergotamine Drugs 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
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000000122 growth hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000007420 reactivation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000035945 sensitivity 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- 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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU3134/76A YU39786B (en) | 1976-12-23 | 1976-12-23 | Process for preparing 2-bromo-alfa-ergocriptine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS215105B2 true CS215105B2 (en) | 1982-07-30 |
Family
ID=25559398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS778043A CS215105B2 (en) | 1976-12-23 | 1977-12-02 | Method of making the 2-brom-alpha-ergocryptin |
Country Status (18)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU216177A (en) | 1977-09-09 | 1984-02-29 | Rudolf Rucman | Process for preparing 2-bromo ergosine |
| YU39849B (en) * | 1978-09-26 | 1985-04-30 | Lek Tovarna Farmacevtskih | Process for preparing 2-bromo-ergolene and 2-bromo-ergoline compounds |
| RU2274640C1 (ru) * | 2004-09-15 | 2006-04-20 | Всероссийский научно-исследовательский институт лекарственных и ароматических растений ("ВИЛАР") | СПОСОБ БРОМИРОВАНИЯ α И β-ЭРГОКРИПТИНОВ |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH507249A (de) * | 1968-05-31 | 1971-05-15 | Sandoz Ag | Verfahren zur Herstellung von 2-Brom-a-ergokryptin |
| YU216177A (en) * | 1977-09-09 | 1984-02-29 | Rudolf Rucman | Process for preparing 2-bromo ergosine |
-
1976
- 1976-12-23 YU YU3134/76A patent/YU39786B/xx unknown
-
1977
- 1977-11-24 DE DE2752532A patent/DE2752532C3/de not_active Expired
- 1977-11-29 PT PT67340A patent/PT67340A/pt unknown
- 1977-11-29 HU HU77LE820A patent/HU176817B/hu unknown
- 1977-12-02 CS CS778043A patent/CS215105B2/cs unknown
- 1977-12-05 JP JP14522377A patent/JPS5384997A/ja active Granted
- 1977-12-07 PL PL1977202697A patent/PL106363B1/pl unknown
- 1977-12-07 GB GB50918/77A patent/GB1574479A/en not_active Expired
- 1977-12-12 RO RO7792428A patent/RO71277A/ro unknown
- 1977-12-13 SU SU772553348A patent/SU795477A3/ru active
- 1977-12-13 UA UA2553348A patent/UA8031A1/uk unknown
- 1977-12-14 DD DD77202623A patent/DD134101A1/xx unknown
- 1977-12-15 ES ES465096A patent/ES465096A1/es not_active Expired
- 1977-12-23 FR FR7738976A patent/FR2375242A1/fr active Granted
-
1985
- 1985-09-20 BE BE1/011337A patent/BE903269Q/fr not_active IP Right Cessation
- 1985-10-02 SG SG718/85A patent/SG71885G/en unknown
- 1985-10-11 KE KE3572A patent/KE3572A/xx unknown
-
1986
- 1986-01-23 HK HK47/86A patent/HK4786A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KE3572A (en) | 1985-11-08 |
| RO71277A (ro) | 1982-02-01 |
| YU313476A (en) | 1982-05-31 |
| DD134101A1 (de) | 1979-02-07 |
| ES465096A1 (es) | 1978-09-01 |
| DE2752532C3 (de) | 1980-09-18 |
| FR2375242B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1983-01-14 |
| HU176817B (en) | 1981-05-28 |
| PL202697A1 (pl) | 1978-07-31 |
| JPS5550038B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-12-16 |
| PT67340A (en) | 1977-12-01 |
| YU39786B (en) | 1985-04-30 |
| JPS5384997A (en) | 1978-07-26 |
| FR2375242A1 (fr) | 1978-07-21 |
| DE2752532B2 (de) | 1979-12-06 |
| SU795477A3 (ru) | 1981-01-07 |
| DE2752532A1 (de) | 1978-06-29 |
| HK4786A (en) | 1986-01-31 |
| GB1574479A (en) | 1980-09-10 |
| BE903269Q (fr) | 1986-01-16 |
| SG71885G (en) | 1988-09-30 |
| UA8031A1 (uk) | 1995-12-26 |
| PL106363B1 (pl) | 1979-12-31 |
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