SE439486B - Syraadditionssalter av hogervridande mjoldrygealkaloider och ett forfarande for framstellning av dessa - Google Patents
Syraadditionssalter av hogervridande mjoldrygealkaloider och ett forfarande for framstellning av dessaInfo
- Publication number
- SE439486B SE439486B SE7906145A SE7906145A SE439486B SE 439486 B SE439486 B SE 439486B SE 7906145 A SE7906145 A SE 7906145A SE 7906145 A SE7906145 A SE 7906145A SE 439486 B SE439486 B SE 439486B
- Authority
- SE
- Sweden
- Prior art keywords
- alkaloids
- methanesulfonate
- ergotamine
- acid addition
- turning
- Prior art date
Links
- 229930013930 alkaloid Natural products 0.000 title claims description 38
- 239000002253 acid Substances 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 13
- 238000000465 moulding Methods 0.000 title 1
- 241000221785 Erysiphales Species 0.000 claims description 25
- 229960004943 ergotamine Drugs 0.000 claims description 23
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- 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 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 19
- HEFIYUQVAZFDEE-UHFFFAOYSA-N ergocristinine Natural products N12C(=O)C(C(C)C)(NC(=O)C3C=C4C=5C=CC=C6NC=C(C=56)CC4N(C)C3)OC2(O)C2CCCN2C(=O)C1CC1=CC=CC=C1 HEFIYUQVAZFDEE-UHFFFAOYSA-N 0.000 claims description 17
- UJYGDMFEEDNVBF-UHFFFAOYSA-N Ergocorninine Natural products C1=CC(C=2C(N(C)CC(C=2)C(=O)NC2(C(=O)N3C(C(N4CCCC4C3(O)O2)=O)C(C)C)C(C)C)C2)=C3C2=CNC3=C1 UJYGDMFEEDNVBF-UHFFFAOYSA-N 0.000 claims description 16
- 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 16
- HEFIYUQVAZFDEE-NASJTFDLSA-N ergocristinine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(N21)=O)(NC(=O)[C@H]1C=C2C=3C=CC=C4NC=C(C=34)C[C@H]2N(C)C1)C(C)C)C1=CC=CC=C1 HEFIYUQVAZFDEE-NASJTFDLSA-N 0.000 claims description 16
- YDOTUXAWKBPQJW-JJANYQHSSA-N 919k69s85n 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-JJANYQHSSA-N 0.000 claims description 15
- NESVMZOPWPCFAU-UHFFFAOYSA-N Ergoclavinine 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)C2)=C3C2=CNC3=C1 NESVMZOPWPCFAU-UHFFFAOYSA-N 0.000 claims description 11
- UJYGDMFEEDNVBF-XJUOHTAZSA-N ergocorninine 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)C(C)C)C(C)C)C2)=C3C2=CNC3=C1 UJYGDMFEEDNVBF-XJUOHTAZSA-N 0.000 claims description 10
- NESVMZOPWPCFAU-UGTZLQJCSA-N ergosinine 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)C2)=C3C2=CNC3=C1 NESVMZOPWPCFAU-UGTZLQJCSA-N 0.000 claims description 9
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- ZXYJWXZEYMJKGE-NRUQAJJTSA-N ergosine methanesulfonate Chemical compound CS(O)(=O)=O.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)C2)=C3C2=CNC3=C1 ZXYJWXZEYMJKGE-NRUQAJJTSA-N 0.000 description 3
- BTLDVNBXSZELNL-DDLCCZDQSA-N ergotamine methansulfonate Chemical compound CS(O)(=O)=O.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=C4NC=C(C=34)C2)=C1)C)C1=CC=CC=C1 BTLDVNBXSZELNL-DDLCCZDQSA-N 0.000 description 3
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- IBTHXSRCPXIAFX-CQVSQEAVSA-N ergocryptinemethanesulfonate 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(OS(C)(=O)=O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=CNC3=C1 IBTHXSRCPXIAFX-CQVSQEAVSA-N 0.000 description 1
- 229960003133 ergot alkaloid Drugs 0.000 description 1
- BTLDVNBXSZELNL-QCQIOXLBSA-N ergotamininemethanesulfonate Chemical compound CS(O)(=O)=O.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=C4NC=C(C=34)C2)=C1)C)C1=CC=CC=C1 BTLDVNBXSZELNL-QCQIOXLBSA-N 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 210000005246 left atrium Anatomy 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- ZAGRKAFMISFKIO-QMTHXVAHSA-N lysergic acid Chemical class C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-QMTHXVAHSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000029865 regulation of blood pressure Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 239000001993 wax Substances 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU1736/78A YU41110B (en) | 1978-07-19 | 1978-07-19 | Process for preparing dextrorotatory ergot alcaloids acid addition salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7906145L SE7906145L (sv) | 1980-01-20 |
| SE439486B true SE439486B (sv) | 1985-06-17 |
Family
ID=25555388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7906145A SE439486B (sv) | 1978-07-19 | 1979-07-16 | Syraadditionssalter av hogervridande mjoldrygealkaloider och ett forfarande for framstellning av dessa |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4440772A (de) |
| JP (1) | JPS5543072A (de) |
| CH (1) | CH641185A5 (de) |
| DE (1) | DE2929027A1 (de) |
| FR (1) | FR2431500A1 (de) |
| GB (1) | GB2025960B (de) |
| PL (1) | PL217433A1 (de) |
| SE (1) | SE439486B (de) |
| YU (1) | YU41110B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH646707A5 (en) * | 1980-03-03 | 1984-12-14 | Richter Gedeon Vegyeszet | Process for the preparation of ergot alkaloids |
| US5069911A (en) * | 1985-02-05 | 1991-12-03 | Sandoz Ltd. | Pharmaceutical 9,10-dihydrogenated ergot alkaloid containing compositions |
| WO1995006280A2 (en) * | 1993-08-26 | 1995-03-02 | Electronic Arts, Inc. | Data transfer accelerating apparatus and method |
| US7771746B2 (en) * | 1999-12-03 | 2010-08-10 | Polichem Sa | Methods for making sustained-release pharmaceutical compositions of ergot alkaloids having improved bioavailability and compositions thereof |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2447214A (en) * | 1948-08-17 | Hoocxchoxxchoxxcooh | ||
| US1435187A (en) * | 1922-11-14 | hzsox | ||
| US2946796A (en) * | 1958-10-15 | 1960-07-26 | Grace W R & Co | Salts of ergot alkaloids |
| GB1011112A (en) * | 1961-05-10 | 1965-11-24 | Sandoz Ag | Improvements in or relating to ergot alkaloids |
| US3314959A (en) * | 1961-05-10 | 1967-04-18 | Sandoz Ltd | Intermediates for the synthesis of ergot alkaloids |
| CH469735A (de) * | 1965-11-02 | 1969-03-15 | Sandoz Ag | Verfahren zur Herstellung heterocyclischer Verbindungen |
| DE1695986A1 (de) * | 1967-02-25 | 1971-05-19 | Dresden Arzneimittel | Verfahren zur Gewinnung der Gesamtalkaloide aus Mutterkorn-Drogen |
| CH520681A (de) * | 1967-08-02 | 1972-03-31 | Sandoz Ag | Verfahren zur Herstellung neuer Mutterkornpeptidalkaloide |
| GB1298277A (en) * | 1969-04-18 | 1972-11-29 | Sandoz Ltd | Preparation of ergot peptide alkaloids |
| US3846433A (en) * | 1969-05-06 | 1974-11-05 | Sandoz Ltd | Process for preparing ergot alkaloids |
| CH619468A5 (de) * | 1976-01-12 | 1980-09-30 | Sandoz Ag |
-
1978
- 1978-07-19 YU YU1736/78A patent/YU41110B/xx unknown
-
1979
- 1979-07-16 SE SE7906145A patent/SE439486B/sv unknown
- 1979-07-17 GB GB7924845A patent/GB2025960B/en not_active Expired
- 1979-07-17 FR FR7918421A patent/FR2431500A1/fr active Granted
- 1979-07-18 CH CH669979A patent/CH641185A5/de not_active IP Right Cessation
- 1979-07-18 DE DE19792929027 patent/DE2929027A1/de not_active Withdrawn
- 1979-07-19 JP JP9106879A patent/JPS5543072A/ja active Pending
- 1979-07-28 PL PL21743379A patent/PL217433A1/xx unknown
-
1981
- 1981-06-02 US US06/269,212 patent/US4440772A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| GB2025960B (en) | 1982-12-15 |
| YU41110B (en) | 1986-12-31 |
| FR2431500A1 (fr) | 1980-02-15 |
| GB2025960A (en) | 1980-01-30 |
| PL217433A1 (de) | 1980-04-08 |
| US4440772A (en) | 1984-04-03 |
| DE2929027A1 (de) | 1980-01-31 |
| FR2431500B1 (de) | 1983-08-05 |
| YU173678A (en) | 1983-01-21 |
| SE7906145L (sv) | 1980-01-20 |
| JPS5543072A (en) | 1980-03-26 |
| CH641185A5 (de) | 1984-02-15 |
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