HU194805B - Process for producing dobuthamine salts - Google Patents
Process for producing dobuthamine salts Download PDFInfo
- Publication number
- HU194805B HU194805B HU854878A HU487885A HU194805B HU 194805 B HU194805 B HU 194805B HU 854878 A HU854878 A HU 854878A HU 487885 A HU487885 A HU 487885A HU 194805 B HU194805 B HU 194805B
- Authority
- HU
- Hungary
- Prior art keywords
- dobutamine
- acid
- water
- salts
- base
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 150000003839 salts Chemical class 0.000 title abstract description 4
- JRWZLRBJNMZMFE-UHFFFAOYSA-N Dobutamine Chemical class C=1C=C(O)C(O)=CC=1CCNC(C)CCC1=CC=C(O)C=C1 JRWZLRBJNMZMFE-UHFFFAOYSA-N 0.000 claims abstract description 30
- 229960001089 dobutamine Drugs 0.000 claims abstract description 20
- 239000002253 acid Substances 0.000 claims abstract description 8
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 12
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 5
- 239000012458 free base Substances 0.000 claims description 5
- 239000011975 tartaric acid Substances 0.000 claims description 5
- 235000002906 tartaric acid Nutrition 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 2
- UOQHWNPVNXSDDO-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=CC(C#N)=CN2C(Br)=CN=C21 UOQHWNPVNXSDDO-UHFFFAOYSA-N 0.000 claims 2
- 229940099563 lactobionic acid Drugs 0.000 claims 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 20
- 206010007625 cardiogenic shock Diseases 0.000 abstract 1
- 238000001990 intravenous administration Methods 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 13
- 239000002585 base Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 7
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 6
- -1 amine salt Chemical class 0.000 description 5
- 229960001654 dobutamine hydrochloride Drugs 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 239000008215 water for injection Substances 0.000 description 3
- WZIUXGZIVZDXIG-WUUYCOTASA-N (2s,3s)-2,3-dihydroxybutanedioic acid;4-[2-[4-(4-hydroxyphenyl)butan-2-ylamino]ethyl]benzene-1,2-diol Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O.C=1C=C(O)C(O)=CC=1CCNC(C)CCC1=CC=C(O)C=C1 WZIUXGZIVZDXIG-WUUYCOTASA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 2
- AEELXMHQIJJMKP-DMTCNVIQSA-N (2r,3s)-3-sulfanylbutane-1,2,4-triol Chemical compound OC[C@@H](O)[C@@H](S)CO AEELXMHQIJJMKP-DMTCNVIQSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- IZXGZAJMDLJLMF-UHFFFAOYSA-N methylaminomethanol Chemical compound CNCO IZXGZAJMDLJLMF-UHFFFAOYSA-N 0.000 description 1
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229940035024 thioglycerol Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
- C07C215/54—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
- C07C59/06—Glycolic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
- C07C59/10—Polyhydroxy carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
- C07C59/10—Polyhydroxy carboxylic acids
- C07C59/105—Polyhydroxy carboxylic acids having five or more carbon atoms, e.g. aldonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
- C07C59/255—Tartaric acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
- C07C59/285—Polyhydroxy dicarboxylic acids having five or more carbon atoms, e.g. saccharic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Detergent Compositions (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Orthopedics, Nursing, And Contraception (AREA)
- Seasonings (AREA)
- Steroid Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68440484A | 1984-12-20 | 1984-12-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT40069A HUT40069A (en) | 1986-11-28 |
| HU194805B true HU194805B (en) | 1988-03-28 |
Family
ID=24747892
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU854878A HU194805B (en) | 1984-12-20 | 1985-12-19 | Process for producing dobuthamine salts |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP0187019B1 (OSRAM) |
| JP (1) | JPS61155355A (OSRAM) |
| KR (1) | KR870000803B1 (OSRAM) |
| CN (1) | CN1009922B (OSRAM) |
| AT (1) | ATE58370T1 (OSRAM) |
| AU (1) | AU589929B2 (OSRAM) |
| CA (1) | CA1254909A (OSRAM) |
| CS (1) | CS253734B2 (OSRAM) |
| DD (1) | DD241071A5 (OSRAM) |
| DE (2) | DE3580575D1 (OSRAM) |
| DK (1) | DK589385A (OSRAM) |
| EG (1) | EG17889A (OSRAM) |
| ES (2) | ES8705841A1 (OSRAM) |
| FI (1) | FI855018A7 (OSRAM) |
| GR (1) | GR853027B (OSRAM) |
| HU (1) | HU194805B (OSRAM) |
| MY (1) | MY104814A (OSRAM) |
| NZ (1) | NZ214583A (OSRAM) |
| PH (1) | PH22547A (OSRAM) |
| PL (1) | PL148296B1 (OSRAM) |
| PT (1) | PT81705B (OSRAM) |
| RO (1) | RO93391B (OSRAM) |
| SU (1) | SU1480761A3 (OSRAM) |
| ZA (1) | ZA859629B (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA881076B (en) * | 1987-02-24 | 1989-10-25 | Lilly Co Eli | Dobutamine salts |
| FR2740337B1 (fr) * | 1995-10-27 | 1997-11-21 | Rhone Poulenc Rorer Sa | Compositions pharmaceutiques stabilisees contenant un derive ayant une activite adrenergique |
| FR2740338B1 (fr) * | 1995-12-01 | 1997-12-05 | Rhone Poulenc Rorer Sa | Compositions pharmaceutiques stabilisees contenant de la dobutamine |
| FR2809619B1 (fr) * | 2000-06-06 | 2004-09-24 | Pharmatop | Nouvelles formulations aqueuses de principes actifs sensibles a l'oxydation et leur procede d'obtention |
| CN105906515B (zh) * | 2015-12-10 | 2018-03-13 | 菏泽市方明制药有限公司 | 一种盐酸多巴酚丁胺脱色工艺 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3987200A (en) * | 1972-04-12 | 1976-10-19 | Eli Lilly And Company | Method for increasing cardiac contractility |
| FR2333499A1 (fr) * | 1975-12-01 | 1977-07-01 | Roussel Uclaf | Nouveau derive de la phenethylamine et ses sels, procede de preparation et application a titre de medicament |
-
1985
- 1985-12-16 RO RO121165A patent/RO93391B/ro unknown
- 1985-12-17 GR GR853027A patent/GR853027B/el unknown
- 1985-12-17 FI FI855018A patent/FI855018A7/fi not_active Application Discontinuation
- 1985-12-17 NZ NZ214583A patent/NZ214583A/xx unknown
- 1985-12-17 PL PL1985256848A patent/PL148296B1/pl unknown
- 1985-12-17 ZA ZA859629A patent/ZA859629B/xx unknown
- 1985-12-18 PT PT81705A patent/PT81705B/pt not_active IP Right Cessation
- 1985-12-18 SU SU853995134A patent/SU1480761A3/ru active
- 1985-12-18 DE DE8585309216T patent/DE3580575D1/de not_active Expired - Lifetime
- 1985-12-18 CA CA000497954A patent/CA1254909A/en not_active Expired
- 1985-12-18 KR KR1019850009534A patent/KR870000803B1/ko not_active Expired
- 1985-12-18 PH PH33213A patent/PH22547A/en unknown
- 1985-12-18 CS CS859449A patent/CS253734B2/cs unknown
- 1985-12-18 DE DE198585309216T patent/DE187019T1/de active Pending
- 1985-12-18 DD DD85284649A patent/DD241071A5/de not_active IP Right Cessation
- 1985-12-18 AT AT85309216T patent/ATE58370T1/de not_active IP Right Cessation
- 1985-12-18 EP EP85309216A patent/EP0187019B1/en not_active Expired - Lifetime
- 1985-12-18 DK DK589385A patent/DK589385A/da not_active Application Discontinuation
- 1985-12-18 EG EG809/85A patent/EG17889A/xx active
- 1985-12-18 AU AU51415/85A patent/AU589929B2/en not_active Ceased
- 1985-12-19 JP JP60287570A patent/JPS61155355A/ja active Granted
- 1985-12-19 ES ES550151A patent/ES8705841A1/es not_active Expired
- 1985-12-19 CN CN85109229A patent/CN1009922B/zh not_active Expired
- 1985-12-19 HU HU854878A patent/HU194805B/hu not_active IP Right Cessation
-
1987
- 1987-02-26 ES ES557426A patent/ES8802570A1/es not_active Expired
- 1987-10-08 MY MYPI87002873A patent/MY104814A/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |