JPS625975A - フロセミド誘導体 - Google Patents
フロセミド誘導体Info
- Publication number
- JPS625975A JPS625975A JP61151855A JP15185586A JPS625975A JP S625975 A JPS625975 A JP S625975A JP 61151855 A JP61151855 A JP 61151855A JP 15185586 A JP15185586 A JP 15185586A JP S625975 A JPS625975 A JP S625975A
- Authority
- JP
- Japan
- Prior art keywords
- furosemide
- formula
- quaternary ammonium
- choline
- betaine
- 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.)
- Pending
Links
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 35
- 229960003883 furosemide Drugs 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- -1 alkylaryl ammonium Chemical compound 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 claims description 7
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 7
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 5
- 229960003237 betaine Drugs 0.000 claims description 5
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 4
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 claims description 3
- 235000019743 Choline chloride Nutrition 0.000 claims description 3
- 229960001231 choline Drugs 0.000 claims description 3
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 claims description 3
- 229960003178 choline chloride Drugs 0.000 claims description 3
- 150000004679 hydroxides Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 150000004820 halides Chemical group 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000009472 formulation Methods 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000004381 Choline salt Substances 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 235000019417 choline salt Nutrition 0.000 description 6
- 239000006186 oral dosage form Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000002934 diuretic Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000001882 diuretic effect Effects 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 229940046250 furosemide injection Drugs 0.000 description 2
- 239000007972 injectable composition Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical compound CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 230000001162 anti-hypercalcemic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 235000013736 caramel Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229940090044 injection Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000006207 intravenous dosage form Substances 0.000 description 1
- 229960004903 invert sugar Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 230000001452 natriuretic effect Effects 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000001508 potassium citrate Substances 0.000 description 1
- 229960002635 potassium citrate Drugs 0.000 description 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
- 235000011082 potassium citrates Nutrition 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000008371 vanilla flavor Substances 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/751,763 US4663348A (en) | 1985-07-02 | 1985-07-02 | Furosemide salts and pharmaceutical preparations thereof |
| US751763 | 1985-07-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS625975A true JPS625975A (ja) | 1987-01-12 |
Family
ID=25023379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61151855A Pending JPS625975A (ja) | 1985-07-02 | 1986-06-30 | フロセミド誘導体 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4663348A (en, 2012) |
| JP (1) | JPS625975A (en, 2012) |
| AU (1) | AU599034B2 (en, 2012) |
| BE (1) | BE904986A (en, 2012) |
| CH (1) | CH670448A5 (en, 2012) |
| DE (1) | DE3619665A1 (en, 2012) |
| DK (1) | DK312586A (en, 2012) |
| FR (1) | FR2584405B1 (en, 2012) |
| GB (1) | GB2189239B (en, 2012) |
| IT (1) | IT1191972B (en, 2012) |
| LU (1) | LU86484A1 (en, 2012) |
| NL (1) | NL8601519A (en, 2012) |
| SE (1) | SE8602917L (en, 2012) |
| ZA (1) | ZA864207B (en, 2012) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5330280A (en) * | 1991-12-03 | 1994-07-19 | Kokuyo Kabushiki Kaisha | Filing apparatus of both-side opening/closing type |
| WO2011099507A1 (ja) * | 2010-02-10 | 2011-08-18 | キッセイ薬品工業株式会社 | 縮合複素環誘導体の塩及びその結晶 |
| JP2016515623A (ja) * | 2013-04-05 | 2016-05-30 | エスシーファーマシューティカルズ インコーポレイテッド | フロセミドの皮下投与用の医薬製剤 |
| US11497755B2 (en) | 2019-01-31 | 2022-11-15 | Scpharmaceuticals Inc. | Concentrated liquid pharmaceutical formulations of furosemide |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4920145A (en) * | 1988-02-29 | 1990-04-24 | Gaf Chemical Corporation | Water-soluble complexes of water-insoluble pharmaceutical compounds and preparation thereof |
| IT1237115B (it) * | 1989-10-24 | 1993-05-18 | Sali della furosemide, procedimento per la loro preparazione e composizionni farmaceutiche che li contengono | |
| US8008283B2 (en) * | 1998-12-23 | 2011-08-30 | Neurotherapeutics Pharma, Inc. | Methods and compositions for the treatment of neuropsychiatric disorders |
| US8722668B2 (en) * | 1998-12-23 | 2014-05-13 | Daryl W. Hochman | Methods and compositions for the treatment of neuropathic pain and neuropsychiatric disorders |
| US7214711B2 (en) * | 1998-12-23 | 2007-05-08 | Neurotherapeutics Pharma Llc | Method of treating migraine headache without aura |
| FI114538B (fi) * | 2001-01-12 | 2004-11-15 | Finnfeeds Finland Ltd | Glysiinibetaiinin käyttö verenpainetta alentavan tuotteen valmistukseen |
| US6989386B2 (en) * | 2002-04-30 | 2006-01-24 | Dana-Farber Cancer Institute | Pharmaceutically active ornithine derivatives, ammonium salts thereof and methods of making same |
| RU2416404C1 (ru) * | 2009-10-05 | 2011-04-20 | Государственное образовательное учреждение высшего профессионального образования "Алтайский государственный медицинский университет Федерального агентства по здравоохранению и социальному развитию" | Средство, обладающее мочегонным действием |
| US11246851B2 (en) | 2019-01-04 | 2022-02-15 | Sq Innovation Ag | Pharmaceutical compositions of furosemide and uses thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3058882A (en) * | 1959-12-28 | 1962-10-16 | Hoechst Ag | N'-substituted-3-carboxy-6-halo-sulfanilamide and derivatives thereof |
| US3565920A (en) * | 1966-12-29 | 1971-02-23 | Ciba Geigy Corp | 5-sulfamyl-anthranilic acids |
| DK138322B (da) * | 1970-07-13 | 1978-08-14 | Dumex Ltd As | Fremgangsmåde til fremstilling af N-substituered antranilsyrederivater. |
| FR2210607A1 (en) * | 1972-12-20 | 1974-07-12 | Aries Robert | 4-Chloro-5-sulphamoyl-N-furfuryl-anthranilic acid prepn. - from furfural and 4-chloro-5-sulphamoyl anthranilic acid |
| DE2343218C2 (de) * | 1973-08-28 | 1986-08-07 | Hoechst Ag, 6230 Frankfurt | Furosemid enthaltende Pellets |
| LU74319A1 (en, 2012) * | 1976-02-09 | 1977-08-19 | ||
| DE3025367A1 (de) * | 1980-07-04 | 1982-01-28 | Hoechst Ag, 6000 Frankfurt | Salz aus furosemid oder piretanid als saeurekomponente und penbutolol oder (-)-3-(4- (3-(3,4-dimethoxyphenylaethylamino)-2-hydroxy-propoxy) -phenyl ) -crotonsaeurenitril als basenkomponente, verfahren zu seiner herstellung, dieses enthaltendes mittel und dessen verwendung |
-
1985
- 1985-07-02 US US06/751,763 patent/US4663348A/en not_active Expired - Fee Related
-
1986
- 1986-06-05 ZA ZA864207A patent/ZA864207B/xx unknown
- 1986-06-11 NL NL8601519A patent/NL8601519A/nl unknown
- 1986-06-11 DE DE19863619665 patent/DE3619665A1/de not_active Withdrawn
- 1986-06-16 AU AU58890/86A patent/AU599034B2/en not_active Ceased
- 1986-06-20 LU LU86484A patent/LU86484A1/fr unknown
- 1986-06-23 FR FR868609017A patent/FR2584405B1/fr not_active Expired
- 1986-06-23 GB GB08615275A patent/GB2189239B/en not_active Expired
- 1986-06-24 BE BE6/48235A patent/BE904986A/fr not_active IP Right Cessation
- 1986-06-25 IT IT48183/86A patent/IT1191972B/it active
- 1986-06-30 JP JP61151855A patent/JPS625975A/ja active Pending
- 1986-07-01 CH CH2639/86A patent/CH670448A5/fr not_active IP Right Cessation
- 1986-07-01 DK DK312586A patent/DK312586A/da not_active Application Discontinuation
- 1986-07-01 SE SE8602917A patent/SE8602917L/xx not_active Application Discontinuation
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5330280A (en) * | 1991-12-03 | 1994-07-19 | Kokuyo Kabushiki Kaisha | Filing apparatus of both-side opening/closing type |
| WO2011099507A1 (ja) * | 2010-02-10 | 2011-08-18 | キッセイ薬品工業株式会社 | 縮合複素環誘導体の塩及びその結晶 |
| CN102753557A (zh) * | 2010-02-10 | 2012-10-24 | 橘生药品工业株式会社 | 稠合杂环衍生物的盐及其晶体 |
| JP5337261B2 (ja) * | 2010-02-10 | 2013-11-06 | キッセイ薬品工業株式会社 | 縮合複素環誘導体の塩及びその結晶 |
| US9169266B2 (en) | 2010-02-10 | 2015-10-27 | Kissei Pharmaceutical Co., Ltd. | Salt of fused heterocyclic derivative and crystal thereof |
| US10576084B2 (en) | 2010-02-10 | 2020-03-03 | Kissei Pharmaceutical Co., Ltd. | Salt of fused heterocyclic derivative and crystal thereof |
| US9737539B2 (en) | 2010-02-10 | 2017-08-22 | Kissei Pharmaceuticals Co., Ltd. | Salt of fused heterocyclic derivative and crystal thereof |
| US10016433B2 (en) | 2010-02-10 | 2018-07-10 | Kissei Pharmaceutical Co., Ltd. | Salt of fused heterocyclic derivative and crystal thereof |
| JP2019001821A (ja) * | 2013-04-05 | 2019-01-10 | エスシーファーマシューティカルズ インコーポレイテッド | フロセミドの皮下投与用の医薬製剤 |
| JP2016515623A (ja) * | 2013-04-05 | 2016-05-30 | エスシーファーマシューティカルズ インコーポレイテッド | フロセミドの皮下投与用の医薬製剤 |
| US11433044B2 (en) | 2013-04-05 | 2022-09-06 | Scpharmaceuticals Inc. | Pharmaceutical formulations for subcutaneous administration of furosemide |
| US12370168B2 (en) | 2013-04-05 | 2025-07-29 | Scpharmaceuticals Inc. | Pharmaceutical formulations for subcutaneous administration of furosemide |
| US11497755B2 (en) | 2019-01-31 | 2022-11-15 | Scpharmaceuticals Inc. | Concentrated liquid pharmaceutical formulations of furosemide |
| US11559535B2 (en) | 2019-01-31 | 2023-01-24 | Scpharmaceuticals Inc. | Concentrated liquid pharmaceutical formulations of furosemide |
| US11571434B2 (en) | 2019-01-31 | 2023-02-07 | Scpharmaceuticals Inc. | Concentrated liquid pharmaceutical formulations of furosemide |
| US11998555B2 (en) | 2019-01-31 | 2024-06-04 | Scpharmaceuticals Inc. | Concentrated liquid pharmaceutical formulations of furosemide and methods of administering the same |
| US12048709B2 (en) | 2019-01-31 | 2024-07-30 | Scpharmaceuticals Inc. | Concentrated liquid pharmaceutical formulations of furosemide and methods of administering the same |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2189239A (en) | 1987-10-21 |
| AU5889086A (en) | 1987-01-08 |
| NL8601519A (nl) | 1987-02-02 |
| DK312586A (da) | 1987-01-03 |
| IT1191972B (it) | 1988-03-31 |
| GB8615275D0 (en) | 1986-07-30 |
| GB2189239B (en) | 1989-02-01 |
| FR2584405B1 (fr) | 1989-02-24 |
| FR2584405A1 (fr) | 1987-01-09 |
| IT8648183A0 (it) | 1986-06-25 |
| DE3619665A1 (de) | 1987-01-08 |
| US4663348A (en) | 1987-05-05 |
| ZA864207B (en) | 1987-02-25 |
| AU599034B2 (en) | 1990-07-12 |
| SE8602917L (sv) | 1987-01-03 |
| BE904986A (fr) | 1986-12-24 |
| SE8602917D0 (sv) | 1986-07-01 |
| LU86484A1 (fr) | 1986-12-02 |
| DK312586D0 (da) | 1986-07-01 |
| CH670448A5 (en, 2012) | 1989-06-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS625975A (ja) | フロセミド誘導体 | |
| JPS6191116A (ja) | 安定化された注射用ピロキシカム液剤 | |
| JPS6064918A (ja) | 消炎剤注射液 | |
| JPS5931713A (ja) | オキシカム誘導体含有医薬組成物 | |
| JPS5869812A (ja) | 血糖降下剤 | |
| US4880835A (en) | Oral liquid pharmaceutical compositions of sulindac | |
| JPS6248678B2 (en, 2012) | ||
| JPS5925377A (ja) | メトロニダゾ−ルとｎ，ｎ−ジメチルグリシンとのエステルおよびその酸付加湿 | |
| KR840000702B1 (ko) | 빈카민 사카리네이트의 제조방법 | |
| US4772589A (en) | Etoposide solution in NMP | |
| HU177873B (en) | Further developped process for preparing an aequous solution containing a complex of n-/3-chloro-4-/4-chloro-phenoxy/-phenyl/-2-hydroxy-3,5-diiodo-benzamide with polyvinyl-pyrrolidone | |
| US2407412A (en) | Therapeutic solutions | |
| JPH0576929B2 (en, 2012) | ||
| JPS6393718A (ja) | 注射剤 | |
| JPH0343251B2 (en, 2012) | ||
| US3906107A (en) | Aminoalkyl sulfate esters with diuretic activity | |
| JP4130700B2 (ja) | 抗腫瘍剤含有組成物 | |
| US2229127A (en) | Sulphanilamide reaction product and process of making it | |
| JP4338517B2 (ja) | グアニジン誘導体の塩及び該塩から成る製薬学的調剤 | |
| JPS5942318A (ja) | 製薬組成物、その製造法及び応用 | |
| KR800000452B1 (ko) | 벤젠설포닐-우레아의 제조방법 | |
| US2755221A (en) | Enhancing solubility of chlorethyltheophylline by nicotinamide and resulting composition | |
| PT86774B (pt) | Processo para a preparacao de fosfatos de dobutamina monobasico | |
| JPH07238019A (ja) | 水溶性タウリン亜鉛化合物 | |
| JPH046705B2 (en, 2012) |