DE3227122C2 - - Google Patents
Info
- Publication number
- DE3227122C2 DE3227122C2 DE3227122A DE3227122A DE3227122C2 DE 3227122 C2 DE3227122 C2 DE 3227122C2 DE 3227122 A DE3227122 A DE 3227122A DE 3227122 A DE3227122 A DE 3227122A DE 3227122 C2 DE3227122 C2 DE 3227122C2
- Authority
- DE
- Germany
- Prior art keywords
- ergot alkaloids
- solutions
- propanediol
- salts
- water
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 17
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229960003133 ergot alkaloid Drugs 0.000 claims abstract description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 9
- 235000013772 propylene glycol Nutrition 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 230000000087 stabilizing effect Effects 0.000 claims abstract description 4
- 239000000654 additive Substances 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims description 4
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 claims description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 2
- 239000003490 Thiodipropionic acid Substances 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- 239000000473 propyl gallate Substances 0.000 claims description 2
- 229940075579 propyl gallate Drugs 0.000 claims description 2
- 235000010388 propyl gallate Nutrition 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 235000019303 thiodipropionic acid Nutrition 0.000 claims description 2
- 239000003791 organic solvent mixture Substances 0.000 claims 1
- 235000019441 ethanol Nutrition 0.000 abstract description 7
- 150000005846 sugar alcohols Polymers 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 4
- 239000011877 solvent mixture Substances 0.000 abstract description 4
- 230000001681 protective effect Effects 0.000 abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000002309 gasification Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 235000011187 glycerol Nutrition 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 3
- 229930013930 alkaloid Natural products 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000008297 liquid dosage form Substances 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 206010022998 Irritability Diseases 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- PBKVEOSEPXMKDN-LZHUFOCISA-N chembl2311030 Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.CS(O)(=O)=O.CS(O)(=O)=O.C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)C(C)C)C(C)C)=C3C2=CNC3=C1.C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)C(C)CC)C(C)C)=C3C2=CNC3=C1.C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)CC(C)C)C(C)C)=C3C2=CNC3=C1.C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(N21)=O)(NC(=O)[C@H]1CN(C)[C@H]2[C@@H](C=3C=CC=C4NC=C(C=34)C2)C1)C(C)C)C1=CC=CC=C1 PBKVEOSEPXMKDN-LZHUFOCISA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- LIMAOLZSWRJOMG-HJPBWRTMSA-N dihydroergocristine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(N21)=O)(NC(=O)[C@H]1CN(C)[C@H]2[C@@H](C3=CC=CC4=NC=C([C]34)C2)C1)C(C)C)C1=CC=CC=C1 LIMAOLZSWRJOMG-HJPBWRTMSA-N 0.000 description 1
- 229960004318 dihydroergocristine Drugs 0.000 description 1
- HESHRHUZIWVEAJ-JGRZULCMSA-N dihydroergotamine 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]2[C@@H](C3=CC=CC4=NC=C([C]34)C2)C1)C)C1=CC=CC=C1 HESHRHUZIWVEAJ-JGRZULCMSA-N 0.000 description 1
- 229960004704 dihydroergotamine Drugs 0.000 description 1
- 230000001037 epileptic effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/48—Ergoline derivatives, e.g. lysergic acid, ergotamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/04—Drugs for genital or sexual disorders; Contraceptives for inducing labour or abortion; Uterotonics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Reproductive Health (AREA)
- Gynecology & Obstetrics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Endocrinology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pregnancy & Childbirth (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823227122 DE3227122A1 (de) | 1982-07-20 | 1982-07-20 | Stabile loesungen von mutterkornalkaloiden |
| JP58101046A JPS5933212A (ja) | 1982-07-20 | 1983-06-08 | 麦角アルカロイド及びその水素化物並びにそれらの塩の安定溶液 |
| EP83107034A EP0101879B2 (de) | 1982-07-20 | 1983-07-18 | Stabile Lösungen von Mutterkornalkaloiden |
| DE8383107034T DE3378892D1 (en) | 1982-07-20 | 1983-07-18 | Stable ergotalcaloids solutions |
| AT83107034T ATE39844T1 (de) | 1982-07-20 | 1983-07-18 | Stabile loesungen von mutterkornalkaloiden. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823227122 DE3227122A1 (de) | 1982-07-20 | 1982-07-20 | Stabile loesungen von mutterkornalkaloiden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3227122A1 DE3227122A1 (de) | 1984-01-26 |
| DE3227122C2 true DE3227122C2 (https=) | 1988-07-14 |
Family
ID=6168867
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823227122 Granted DE3227122A1 (de) | 1982-07-20 | 1982-07-20 | Stabile loesungen von mutterkornalkaloiden |
| DE8383107034T Expired DE3378892D1 (en) | 1982-07-20 | 1983-07-18 | Stable ergotalcaloids solutions |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8383107034T Expired DE3378892D1 (en) | 1982-07-20 | 1983-07-18 | Stable ergotalcaloids solutions |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0101879B2 (https=) |
| JP (1) | JPS5933212A (https=) |
| AT (1) | ATE39844T1 (https=) |
| DE (2) | DE3227122A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1200609B (it) * | 1985-04-04 | 1989-01-27 | Poli Ind Chimica Spa | Composizione farmaceutice per il trattamento delle turbe cerebrovascolari e del cervello anziano |
| AT381232B (de) * | 1985-05-13 | 1986-09-10 | Kwizda Fa F Johann | Verfahren zur herstellung stabiler fluessiger loesungen von ergolinderivaten |
| DE3710216A1 (de) * | 1987-03-27 | 1988-10-06 | Rentschler Arzneimittel | Verwendung von dihydroergotamin und seinen salzen zur lokalen behandlung trophischer stoerungen |
| WO2000057851A2 (en) * | 1999-03-26 | 2000-10-05 | Pozen Inc. | High potency dihydroergotamine compositions |
| JP4558995B2 (ja) | 2001-09-12 | 2010-10-06 | ベックマン コールター， インコーポレイテッド | 移送ユニットおよびその移送ユニットを備える自動分析装置 |
| DE102007014947B4 (de) | 2007-03-23 | 2010-05-27 | Axxonis Pharma Ag | Stabilisierte wässrige Lösungen von Ergolinverbindungen |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD43402A (https=) * | ||||
| GB1175430A (en) * | 1966-04-07 | 1969-12-23 | Sandoz Ltd | Pharmaceutical Compositions containing Ergot Alkaloids |
| GB1494625A (en) * | 1974-02-04 | 1977-12-07 | Unilever Ltd | Pharmaceutical preparations |
| DK147775A (https=) * | 1974-04-16 | 1975-10-17 | Sandoz Ag | |
| DE2518677A1 (de) * | 1974-05-06 | 1975-11-20 | Sandoz Ag | Neue pharmazeutische zubereitungen |
| FI761461A7 (https=) * | 1975-05-31 | 1976-12-01 | Sandoz Ag | |
| DE2735587A1 (de) * | 1977-08-06 | 1979-02-15 | Sandoz Ag | Stabile loesungen und verfahren zu deren herstellung |
| DE2555481C3 (de) * | 1975-12-10 | 1985-10-03 | Sandoz-Patent-GmbH, 7850 Lörrach | Herstellung stabiler Tropflösungen von hydrierten Ergotalkaloiden |
| DE2945636A1 (de) * | 1979-11-12 | 1981-05-21 | Sandoz-Patent-GmbH, 7850 Lörrach | Stabile loesungen von hydrierten ergotalkaloiden bzw. ihren salzen und heparin bzw. seinen salzen sowie verfahren zu deren herstellung |
| BE880542A (fr) * | 1979-12-11 | 1980-06-11 | Christiaens Sa A | Solutions aqueuses stables d'alcaloides de l'ergot de seigle |
| JPS5795907A (en) * | 1980-10-15 | 1982-06-15 | Rentschler Arzneimittel | Liquid medicine of ergot alkaloid |
-
1982
- 1982-07-20 DE DE19823227122 patent/DE3227122A1/de active Granted
-
1983
- 1983-06-08 JP JP58101046A patent/JPS5933212A/ja active Pending
- 1983-07-18 DE DE8383107034T patent/DE3378892D1/de not_active Expired
- 1983-07-18 AT AT83107034T patent/ATE39844T1/de not_active IP Right Cessation
- 1983-07-18 EP EP83107034A patent/EP0101879B2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5933212A (ja) | 1984-02-23 |
| EP0101879A2 (de) | 1984-03-07 |
| DE3378892D1 (en) | 1989-02-16 |
| EP0101879A3 (en) | 1985-04-03 |
| EP0101879B1 (de) | 1989-01-11 |
| EP0101879B2 (de) | 1993-11-10 |
| ATE39844T1 (de) | 1989-01-15 |
| DE3227122A1 (de) | 1984-01-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OM8 | Search report available as to paragraph 43 lit. 1 sentence 1 patent law | ||
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8363 | Opposition against the patent | ||
| 8365 | Fully valid after opposition proceedings | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: DR. RENTSCHLER GMBH & CO. MEDIZIN KG, 88471 LAUPHE |