CH625792A5 - - Google Patents
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- Publication number
- CH625792A5 CH625792A5 CH149777A CH149777A CH625792A5 CH 625792 A5 CH625792 A5 CH 625792A5 CH 149777 A CH149777 A CH 149777A CH 149777 A CH149777 A CH 149777A CH 625792 A5 CH625792 A5 CH 625792A5
- Authority
- CH
- Switzerland
- Prior art keywords
- salt
- formula
- urapidil
- hypertension
- iii
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 claims description 16
- -1 piperazinopropylaminouracil salt Chemical class 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 6
- 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 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 206010020772 Hypertension Diseases 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ICMGLRUYEQNHPF-UHFFFAOYSA-N Uraprene Chemical compound COC1=CC=CC=C1N1CCN(CCCNC=2N(C(=O)N(C)C(=O)C=2)C)CC1 ICMGLRUYEQNHPF-UHFFFAOYSA-N 0.000 description 6
- 229960001130 urapidil Drugs 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 229960003883 furosemide Drugs 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 238000010606 normalization Methods 0.000 description 2
- 125000006308 propyl amino group Chemical group 0.000 description 2
- 239000011833 salt mixture Substances 0.000 description 2
- 238000009938 salting Methods 0.000 description 2
- 229940035893 uracil Drugs 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- HTTFZDUQAOQWTC-UHFFFAOYSA-N 3-amino-4-chloro-2-(furan-2-ylmethyl)-5-sulfamoylbenzoic acid Chemical compound NC1=C(Cl)C(S(N)(=O)=O)=CC(C(O)=O)=C1CC1=CC=CO1 HTTFZDUQAOQWTC-UHFFFAOYSA-N 0.000 description 1
- 208000007530 Essential hypertension Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 201000004239 Secondary hypertension Diseases 0.000 description 1
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Natural products O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
-
- 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
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU74319A LU74319A1 (en, 2012) | 1976-02-09 | 1976-02-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH625792A5 true CH625792A5 (en, 2012) | 1981-10-15 |
Family
ID=19728151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH149777A CH625792A5 (en, 2012) | 1976-02-09 | 1977-02-08 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4131678A (en, 2012) |
| JP (2) | JPS5296718A (en, 2012) |
| AT (1) | AT347478B (en, 2012) |
| BE (1) | BE851267A (en, 2012) |
| CA (1) | CA1065865A (en, 2012) |
| CH (1) | CH625792A5 (en, 2012) |
| DE (1) | DE2704935C2 (en, 2012) |
| DK (1) | DK52877A (en, 2012) |
| ES (1) | ES455721A1 (en, 2012) |
| FI (1) | FI61891C (en, 2012) |
| FR (1) | FR2340316A1 (en, 2012) |
| GB (1) | GB1512771A (en, 2012) |
| IE (1) | IE44461B1 (en, 2012) |
| IL (1) | IL51400A (en, 2012) |
| IT (1) | IT1075919B (en, 2012) |
| LU (1) | LU74319A1 (en, 2012) |
| NL (1) | NL7701289A (en, 2012) |
| NO (1) | NO145440C (en, 2012) |
| SE (1) | SE7701441L (en, 2012) |
| YU (1) | YU32477A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0452107A1 (en) * | 1990-04-13 | 1991-10-16 | MITSUI TOATSU CHEMICALS, Inc. | Pyrimidinedione derivatives and antiarrythmic agents containing same |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58130183U (ja) * | 1982-02-26 | 1983-09-02 | 株式会社ブレスト工業研究所 | 空調ダクト等の吊持装置 |
| US4663348A (en) * | 1985-07-02 | 1987-05-05 | Warner-Lambert Co. | Furosemide salts and pharmaceutical preparations thereof |
| IE62890B1 (en) * | 1988-12-06 | 1995-03-08 | Hafslund Nycomed Pharma | New piperazinylalkyl-3(2h)-pyridazinones process for the preparation thereof and the use thereof as agents lowering blood pressure |
| DE3902316A1 (de) * | 1989-01-26 | 1990-08-02 | Lentia Gmbh | Neue piperazinylalkyl-3(2h)-pyridazinone, verfahren zu ihrer herstellung und ihre verwendung als blutdrucksenkende mittel |
| CN100353944C (zh) * | 2004-06-24 | 2007-12-12 | 杨立新 | 乌拉地尔大容量注射液、其制备方法及其应用 |
Family Cites Families (3)
| 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 |
| BE755015A (fr) * | 1969-08-20 | 1971-02-01 | Byk Gulden Lomberg Chem Fab | Piperazinyl-alcoylamino-uraciles substitues par un groupe aryle, leurs ethers et thioethers, ainsi que leur procede de preparation |
| JPS5212560A (en) * | 1975-07-21 | 1977-01-31 | Hitachi Ltd | Electronic beam probe control device |
-
1976
- 1976-02-09 LU LU74319A patent/LU74319A1/xx unknown
-
1977
- 1977-02-07 IL IL51400A patent/IL51400A/xx unknown
- 1977-02-07 GB GB4900/77A patent/GB1512771A/en not_active Expired
- 1977-02-07 DE DE2704935A patent/DE2704935C2/de not_active Expired
- 1977-02-07 YU YU00324/77A patent/YU32477A/xx unknown
- 1977-02-08 DK DK52877A patent/DK52877A/da unknown
- 1977-02-08 AT AT81777A patent/AT347478B/de not_active IP Right Cessation
- 1977-02-08 CH CH149777A patent/CH625792A5/de not_active IP Right Cessation
- 1977-02-08 ES ES455721A patent/ES455721A1/es not_active Expired
- 1977-02-08 NL NL7701289A patent/NL7701289A/xx not_active Application Discontinuation
- 1977-02-08 IE IE257/77A patent/IE44461B1/en unknown
- 1977-02-08 IT IT20045/77A patent/IT1075919B/it active
- 1977-02-08 CA CA271,351A patent/CA1065865A/en not_active Expired
- 1977-02-08 FI FI770406A patent/FI61891C/fi not_active IP Right Cessation
- 1977-02-08 NO NO770411A patent/NO145440C/no unknown
- 1977-02-09 JP JP1256077A patent/JPS5296718A/ja active Granted
- 1977-02-09 FR FR7703584A patent/FR2340316A1/fr active Granted
- 1977-02-09 BE BE6045873A patent/BE851267A/xx unknown
- 1977-02-09 SE SE7701441A patent/SE7701441L/xx not_active Application Discontinuation
- 1977-02-09 US US05/767,214 patent/US4131678A/en not_active Expired - Lifetime
-
1981
- 1981-06-10 JP JP8831781A patent/JPS5726618A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0452107A1 (en) * | 1990-04-13 | 1991-10-16 | MITSUI TOATSU CHEMICALS, Inc. | Pyrimidinedione derivatives and antiarrythmic agents containing same |
Also Published As
| Publication number | Publication date |
|---|---|
| ATA81777A (de) | 1978-05-15 |
| NO145440B (no) | 1981-12-14 |
| FI770406A7 (en, 2012) | 1977-08-10 |
| IL51400A (en) | 1980-12-31 |
| BE851267A (fr) | 1977-08-09 |
| DE2704935C2 (de) | 1985-01-10 |
| FR2340316B1 (en, 2012) | 1980-02-08 |
| NO145440C (no) | 1982-03-24 |
| YU32477A (en) | 1982-06-30 |
| GB1512771A (en) | 1978-06-01 |
| AT347478B (de) | 1978-12-27 |
| JPS5713544B2 (en, 2012) | 1982-03-17 |
| ES455721A1 (es) | 1978-01-01 |
| JPS5726618A (en) | 1982-02-12 |
| DE2704935A1 (de) | 1977-08-11 |
| IE44461L (en) | 1977-08-09 |
| NL7701289A (nl) | 1977-08-11 |
| FI61891B (fi) | 1982-06-30 |
| FR2340316A1 (fr) | 1977-09-02 |
| IL51400A0 (en) | 1977-04-29 |
| JPS5296718A (en) | 1977-08-13 |
| CA1065865A (en) | 1979-11-06 |
| SE7701441L (sv) | 1977-08-10 |
| NO770411L (no) | 1977-08-10 |
| IT1075919B (it) | 1985-04-22 |
| LU74319A1 (en, 2012) | 1977-08-19 |
| FI61891C (fi) | 1982-10-11 |
| IE44461B1 (en) | 1981-12-02 |
| DK52877A (da) | 1977-08-10 |
| US4131678A (en) | 1978-12-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |