NO134153B - - Google Patents
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- Publication number
- NO134153B NO134153B NO1719/72A NO171972A NO134153B NO 134153 B NO134153 B NO 134153B NO 1719/72 A NO1719/72 A NO 1719/72A NO 171972 A NO171972 A NO 171972A NO 134153 B NO134153 B NO 134153B
- Authority
- NO
- Norway
- Prior art keywords
- mol
- methanol
- formula
- filtration
- dried
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- WYFKHRKLNSAEBW-UHFFFAOYSA-N n-[2-(hydroxyamino)-2-oxoethyl]benzamide Chemical class ONC(=O)CNC(=O)C1=CC=CC=C1 WYFKHRKLNSAEBW-UHFFFAOYSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 208000006568 Urinary Bladder Calculi Diseases 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000588770 Proteus mirabilis Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 229960000723 ampicillin Drugs 0.000 description 2
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002648 combination therapy Methods 0.000 description 2
- XYVZUPHHGNHQHN-UHFFFAOYSA-N ethyl 2-[(4-chlorobenzoyl)amino]acetate Chemical compound CCOC(=O)CNC(=O)C1=CC=C(Cl)C=C1 XYVZUPHHGNHQHN-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229960000564 nitrofurantoin Drugs 0.000 description 2
- NXFQHRVNIOXGAQ-YCRREMRBSA-N nitrofurantoin Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)NC(=O)C1 NXFQHRVNIOXGAQ-YCRREMRBSA-N 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229960005404 sulfamethoxazole Drugs 0.000 description 2
- JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 210000001635 urinary tract Anatomy 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- COYZIYOEXGRBHQ-UHFFFAOYSA-N 2-[(4-chlorobenzoyl)amino]acetic acid Chemical compound OC(=O)CNC(=O)C1=CC=C(Cl)C=C1 COYZIYOEXGRBHQ-UHFFFAOYSA-N 0.000 description 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000219733 Lathyrus hirsutus Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 108010046334 Urease Proteins 0.000 description 1
- RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 description 1
- 229960001171 acetohydroxamic acid Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- MXZRMHIULZDAKC-UHFFFAOYSA-L ammonium magnesium phosphate Chemical compound [NH4+].[Mg+2].[O-]P([O-])([O-])=O MXZRMHIULZDAKC-UHFFFAOYSA-L 0.000 description 1
- JFZGBMJPJZDNNT-UHFFFAOYSA-N benurestat Chemical compound ONC(=O)CNC(=O)C1=CC=C(Cl)C=C1 JFZGBMJPJZDNNT-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- -1 ester hydrochloride Chemical class 0.000 description 1
- FGQTXDKZTAZFRS-UHFFFAOYSA-N ethyl 2-[(4-nitrobenzoyl)amino]acetate Chemical compound CCOC(=O)CNC(=O)C1=CC=C([N+]([O-])=O)C=C1 FGQTXDKZTAZFRS-UHFFFAOYSA-N 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- AYRMIJUZZRHLNH-UHFFFAOYSA-N n-[2-(hydroxyamino)-2-oxoethyl]-4-nitrobenzamide Chemical compound ONC(=O)CNC(=O)C1=CC=C([N+]([O-])=O)C=C1 AYRMIJUZZRHLNH-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000005000 reproductive tract Anatomy 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 208000019206 urinary tract infection Diseases 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
- A61K31/13—Amines
- A61K31/15—Oximes (>C=N—O—); Hydrazines (>N—N<); Hydrazones (>N—N=) ; Imines (C—N=C)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14432271A | 1971-05-17 | 1971-05-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO134153B true NO134153B (sl) | 1976-05-18 |
| NO134153C NO134153C (sl) | 1976-08-25 |
Family
ID=22508076
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1719/72A NO134153C (sl) | 1971-05-17 | 1972-05-15 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3728380A (sl) |
| AR (1) | AR192778A1 (sl) |
| AT (1) | AT311939B (sl) |
| AU (1) | AU456216B2 (sl) |
| BE (1) | BE783541A (sl) |
| CA (1) | CA1003852A (sl) |
| CH (1) | CH565755A5 (sl) |
| DE (1) | DE2223857A1 (sl) |
| DK (1) | DK130959B (sl) |
| ES (1) | ES402670A1 (sl) |
| FR (1) | FR2137966B1 (sl) |
| GB (1) | GB1335363A (sl) |
| IL (1) | IL39347A (sl) |
| NL (1) | NL7206589A (sl) |
| NO (1) | NO134153C (sl) |
| SE (2) | SE376605B (sl) |
| ZA (1) | ZA723158B (sl) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4077998A (en) * | 1975-10-28 | 1978-03-07 | Morton-Norwich Products, Inc. | Phthaloyl amino acid hydroxamic acids |
| US4083996A (en) * | 1976-02-20 | 1978-04-11 | Eisai Co., Ltd. | Novel hydroxamic acid derivatives and medicaments for treatment of urolithiasis and pyelonephrosis comprising such derivatives |
| US4157396A (en) * | 1976-02-20 | 1979-06-05 | Eisai Co., Ltd. | Hydroxamic acid derivatives and medicaments for treatment of urolithiasis and pyelonephrosis comprising such derivatives |
| GB1574822A (en) * | 1976-03-23 | 1980-09-10 | Lafon Labor | Acetohydroxamic acid derivatives and pharmaceutical compositions thereof |
| FR2502617B1 (sl) * | 1981-03-25 | 1984-04-27 | Lafon Labor | |
| IT1283637B1 (it) * | 1996-05-14 | 1998-04-23 | Italfarmaco Spa | Composti ad attivita' antinfiammatoria ed immunosoppressiva |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2279560A (en) * | 1940-05-08 | 1942-04-14 | Du Pont | Viscous hydrocarbon oil |
| US2279973A (en) * | 1940-05-08 | 1942-04-14 | Du Pont | Stabilization of organic substances |
| GB1048936A (en) * | 1962-06-07 | 1966-11-23 | Fisons Pest Control Ltd | Cinnamylidene compounds |
| US3444232A (en) * | 1966-05-18 | 1969-05-13 | Squibb & Sons Inc | O-alkyl or phenylalkyl benzohydroxamic acids |
| US3634509A (en) * | 1966-06-08 | 1972-01-11 | Shell Oil Co | 2 6-dinitroanilinoacetamides |
-
1971
- 1971-05-17 US US00144322A patent/US3728380A/en not_active Expired - Lifetime
-
1972
- 1972-05-03 IL IL39347A patent/IL39347A/xx unknown
- 1972-05-03 AU AU41820/72A patent/AU456216B2/en not_active Expired
- 1972-05-09 ZA ZA723158A patent/ZA723158B/xx unknown
- 1972-05-12 ES ES402670A patent/ES402670A1/es not_active Expired
- 1972-05-15 NO NO1719/72A patent/NO134153C/no unknown
- 1972-05-16 DE DE19722223857 patent/DE2223857A1/de active Pending
- 1972-05-16 CA CA142,316A patent/CA1003852A/en not_active Expired
- 1972-05-16 NL NL7206589A patent/NL7206589A/xx unknown
- 1972-05-16 DK DK242072AA patent/DK130959B/da unknown
- 1972-05-16 BE BE783541A patent/BE783541A/xx unknown
- 1972-05-16 AR AR242018A patent/AR192778A1/es active
- 1972-05-16 SE SE7206353A patent/SE376605B/xx unknown
- 1972-05-16 AT AT426072A patent/AT311939B/de not_active IP Right Cessation
- 1972-05-16 SE SE7406597A patent/SE389018B/xx unknown
- 1972-05-16 FR FR7217481A patent/FR2137966B1/fr not_active Expired
- 1972-05-17 CH CH733672A patent/CH565755A5/xx not_active IP Right Cessation
- 1972-05-17 GB GB2309572A patent/GB1335363A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE783541A (fr) | 1972-11-16 |
| FR2137966B1 (sl) | 1975-12-26 |
| AU456216B2 (en) | 1974-12-12 |
| AT311939B (de) | 1973-12-10 |
| NL7206589A (sl) | 1972-11-21 |
| GB1335363A (en) | 1973-10-24 |
| NO134153C (sl) | 1976-08-25 |
| IL39347A0 (en) | 1972-07-26 |
| CA1003852A (en) | 1977-01-18 |
| CH565755A5 (sl) | 1975-08-29 |
| AR192778A1 (es) | 1973-03-14 |
| SE376605B (sl) | 1975-06-02 |
| IL39347A (en) | 1975-03-13 |
| US3728380A (en) | 1973-04-17 |
| FR2137966A1 (sl) | 1972-12-29 |
| ZA723158B (en) | 1973-12-19 |
| AU4182072A (en) | 1973-11-08 |
| SE389018B (sv) | 1976-10-25 |
| DE2223857A1 (de) | 1972-12-07 |
| DK130959C (sl) | 1975-10-13 |
| ES402670A1 (es) | 1975-11-01 |
| DK130959B (da) | 1975-05-12 |
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