CH544053A - Verfahren zur Herstellung von Sulfonamidderivaten - Google Patents
Verfahren zur Herstellung von SulfonamidderivatenInfo
- Publication number
- CH544053A CH544053A CH280973A CH280973A CH544053A CH 544053 A CH544053 A CH 544053A CH 280973 A CH280973 A CH 280973A CH 280973 A CH280973 A CH 280973A CH 544053 A CH544053 A CH 544053A
- Authority
- CH
- Switzerland
- Prior art keywords
- pyrimidine
- dimethoxy
- sulfanilamido
- solutions
- dissolved
- Prior art date
Links
- 229940124530 sulfonamide Drugs 0.000 title claims abstract description 29
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 title abstract 3
- MAIVCOSUIAQGHY-UHFFFAOYSA-N 4-amino-2,3-dimethoxy-n-pyrimidin-2-ylbenzenesulfonamide Chemical compound COC1=C(N)C=CC(S(=O)(=O)NC=2N=CC=CN=2)=C1OC MAIVCOSUIAQGHY-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 8
- NHUHCSRWZMLRLA-UHFFFAOYSA-N Sulfisoxazole Chemical compound CC1=NOC(NS(=O)(=O)C=2C=CC(N)=CC=2)=C1C NHUHCSRWZMLRLA-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000243 solution Substances 0.000 claims description 37
- 150000003456 sulfonamides Chemical class 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 238000002347 injection Methods 0.000 claims description 10
- 239000007924 injection Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- ZZORFUFYDOWNEF-UHFFFAOYSA-N sulfadimethoxine Chemical compound COC1=NC(OC)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ZZORFUFYDOWNEF-UHFFFAOYSA-N 0.000 claims description 4
- JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 0.000 claims description 3
- 239000008346 aqueous phase Substances 0.000 claims description 2
- 235000020354 squash Nutrition 0.000 claims description 2
- ASWVTGNCAZCNNR-UHFFFAOYSA-N sulfamethazine Chemical compound CC1=CC(C)=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ASWVTGNCAZCNNR-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 8
- -1 aryl 2,4-diamino-5-(3,4-dimethoxybenzyl)-pyrimidine Chemical group 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- DZHKPVJNIUOWTI-UHFFFAOYSA-N 2-amino-4,6-dimethoxy-n-pyrimidin-2-ylbenzenesulfonamide Chemical compound COC1=CC(OC)=CC(N)=C1S(=O)(=O)NC1=NC=CC=N1 DZHKPVJNIUOWTI-UHFFFAOYSA-N 0.000 abstract 1
- IMSKSJKAEYLZJH-UHFFFAOYSA-N 2-amino-4,6-dimethyl-n-pyrimidin-2-ylbenzenesulfonamide Chemical compound NC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=NC=CC=N1 IMSKSJKAEYLZJH-UHFFFAOYSA-N 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 239000012153 distilled water Substances 0.000 description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 229940074076 glycerol formal Drugs 0.000 description 9
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 9
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 229920000151 polyglycol Polymers 0.000 description 8
- 239000010695 polyglycol Substances 0.000 description 8
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- 239000003814 drug Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- KEEYRKYKLYARHO-UHFFFAOYSA-N 5-[(4,5-dimethoxy-2-methylphenyl)methyl]pyrimidine-2,4-diamine Chemical compound C1=C(OC)C(OC)=CC(C)=C1CC1=CN=C(N)N=C1N KEEYRKYKLYARHO-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- LDBTVAXGKYIFHO-UHFFFAOYSA-N diaveridine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=CN=C(N)N=C1N LDBTVAXGKYIFHO-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- VCKSNYNNVSOWEE-UHFFFAOYSA-N 1,3-dioxan-5-ol Chemical compound OC1COCOC1 VCKSNYNNVSOWEE-UHFFFAOYSA-N 0.000 description 1
- BOHGAOWOIJMTPZ-UHFFFAOYSA-N 1,3-dioxolan-4-ylmethanol Chemical compound OCC1COCO1 BOHGAOWOIJMTPZ-UHFFFAOYSA-N 0.000 description 1
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- IEAAAQXTROJCRL-UHFFFAOYSA-N 5-[(2,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound COC1=CC(OC)=C(OC)C=C1CC1=CN=C(N)N=C1N IEAAAQXTROJCRL-UHFFFAOYSA-N 0.000 description 1
- PVQOGQNECOHWIH-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-6-ethylpyrimidine-2,4-diamine Chemical compound CCC1=NC(N)=NC(N)=C1CC1=CC=C(Cl)C=C1 PVQOGQNECOHWIH-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000011221 initial treatment Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- 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
- A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
- A61K31/635—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide having a heterocyclic ring, e.g. sulfadiazine
-
- 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
- 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
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
-
- 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
- A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
-
- 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
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Electric Connection Of Electric Components To Printed Circuits (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH280973A CH544053A (de) | 1966-05-09 | 1966-05-09 | Verfahren zur Herstellung von Sulfonamidderivaten |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH671666 | 1966-05-09 | ||
| CH280973A CH544053A (de) | 1966-05-09 | 1966-05-09 | Verfahren zur Herstellung von Sulfonamidderivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH544053A true CH544053A (de) | 1973-11-15 |
Family
ID=74187416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH280973A CH544053A (de) | 1966-05-09 | 1966-05-09 | Verfahren zur Herstellung von Sulfonamidderivaten |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3551564A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS5017524B1 (cg-RX-API-DMAC7.html) |
| BE (1) | BE698102A (cg-RX-API-DMAC7.html) |
| CH (1) | CH544053A (cg-RX-API-DMAC7.html) |
| DE (1) | DE1617521C3 (cg-RX-API-DMAC7.html) |
| DK (1) | DK117520B (cg-RX-API-DMAC7.html) |
| ES (1) | ES340262A1 (cg-RX-API-DMAC7.html) |
| FI (1) | FI48975C (cg-RX-API-DMAC7.html) |
| FR (1) | FR1523606A (cg-RX-API-DMAC7.html) |
| GB (1) | GB1176395A (cg-RX-API-DMAC7.html) |
| GR (1) | GR35814B (cg-RX-API-DMAC7.html) |
| IL (1) | IL27876A (cg-RX-API-DMAC7.html) |
| IT (1) | IT1143624B (cg-RX-API-DMAC7.html) |
| NL (1) | NL140736B (cg-RX-API-DMAC7.html) |
| NO (1) | NO127486B (cg-RX-API-DMAC7.html) |
| SE (1) | SE348112B (cg-RX-API-DMAC7.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0037501A1 (de) * | 1980-03-25 | 1981-10-14 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Pharmazeutische Präparate und deren Herstellung |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZM3271A1 (en) * | 1970-03-13 | 1972-10-23 | Wellcome Found | Improvements in or relating to injectable therapeutic compositions |
| US3728452A (en) * | 1971-01-20 | 1973-04-17 | Abic Ltd | Water-soluble composition comprising sulfadimidine and pyrimethamine |
| IT1044231B (it) * | 1972-03-16 | 1980-03-20 | Hoffmann La Roche | Combinazione di sostanze attive utile per combattere infezioni da batteri gram positivi e gran negativi |
| DE2342213C3 (de) * | 1972-10-12 | 1979-10-18 | F. Hoffmann-La Roche & Co Ag, Basel (Schweiz) | Verwendung von potenzierten SuIf onamiden bei der Behandlung oder Verhinderung von Fischinfektionen |
| US3985876A (en) * | 1973-01-05 | 1976-10-12 | Burroughs Wellcome Co. | Chemotherapeutic solutions containing a sulphur and a salt of a 2,4-diamino-5-benzylpyrimidine |
| GB1485383A (en) * | 1973-09-24 | 1977-09-08 | Wellcome Found | Injectable non-aqueous therapeutic compositions |
| GB1485382A (en) * | 1973-09-24 | 1977-09-08 | Wellcome Found | Injectable therapeutic compositions |
| US4039543A (en) * | 1974-12-24 | 1977-08-02 | Hoffmann-La Roche Inc. | Benzylpyrimidines |
| DK136934B (da) * | 1976-02-06 | 1977-12-19 | Rosco As | Fremgangsmåde til fremstilling af en klar, stabil, injicerbar opløsning indeholdende et sulfonamid og en potentiator. |
| DE2631780C3 (de) * | 1976-07-15 | 1981-11-19 | Basf Ag, 6700 Ludwigshafen | Sulfonamid-Trimethoprim-Lösungen |
| DE2731013C2 (de) * | 1977-07-08 | 1982-07-15 | Lentia Gmbh | Verfahren zur Herstellung einer wäßrigen Infusionslösung |
| JPS54154775A (en) * | 1978-05-24 | 1979-12-06 | Wellcome Found | Benzylpyrimidine derivative |
| DE2963408D1 (en) | 1978-08-01 | 1982-09-16 | Ciba Geigy Ag | Stable medicinal solution on the basis of 2,6-diamino-5-(3',4',5'-trimethoxybenzyl)-pyrimidine(trimethoprim) and a sulphonamide, process for preparing and using it |
| US4303643A (en) * | 1979-07-05 | 1981-12-01 | Pfizer Inc. | Sulfonamide compositions |
| HU180740B (en) * | 1979-11-27 | 1983-04-29 | Egyt Gyogyszervegyeszeti Gyar | Process for producing sulfonamide-containing,injectable pharmaceutical composition of prolongated activity |
| AR220263A1 (es) * | 1980-02-19 | 1980-10-15 | Bago Lab Sa | Procedimiento para obtener una preparacion inyectable de sulfonamida potenciada de baja irritabilidad |
| US4374826A (en) * | 1980-07-21 | 1983-02-22 | Pfizer Inc. | Sulfonamide compositions |
| EP4417701A4 (en) * | 2021-10-12 | 2025-03-05 | Daan Gene Co., Ltd. | IN VITRO PRESERVATIVES FOR DIAGNOSTIC REAGENTS AND USE THEREOF |
-
1966
- 1966-05-09 CH CH280973A patent/CH544053A/de not_active IP Right Cessation
-
1967
- 1967-04-24 DE DE1617521A patent/DE1617521C3/de not_active Expired
- 1967-04-28 IL IL27876A patent/IL27876A/xx unknown
- 1967-04-28 US US634472A patent/US3551564A/en not_active Expired - Lifetime
- 1967-05-03 FI FI671280A patent/FI48975C/fi active
- 1967-05-08 ES ES340262A patent/ES340262A1/es not_active Expired
- 1967-05-08 BE BE698102D patent/BE698102A/xx not_active IP Right Cessation
- 1967-05-08 NO NO00168048A patent/NO127486B/no unknown
- 1967-05-08 DK DK241967AA patent/DK117520B/da not_active IP Right Cessation
- 1967-05-08 JP JP42028760A patent/JPS5017524B1/ja active Pending
- 1967-05-08 FR FR105482A patent/FR1523606A/fr not_active Expired
- 1967-05-08 SE SE06386/67A patent/SE348112B/xx unknown
- 1967-05-08 GR GR670135814A patent/GR35814B/el unknown
- 1967-05-08 GB GB21230/67A patent/GB1176395A/en not_active Expired
- 1967-05-09 NL NL676706474A patent/NL140736B/xx not_active IP Right Cessation
- 1967-05-09 IT IT15891/67A patent/IT1143624B/it active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0037501A1 (de) * | 1980-03-25 | 1981-10-14 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Pharmazeutische Präparate und deren Herstellung |
| US4532245A (en) * | 1980-03-25 | 1985-07-30 | Hoffmann-La Roche Inc. | Pharmaceutical compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| SE348112B (cg-RX-API-DMAC7.html) | 1972-08-28 |
| FI48975C (fi) | 1975-03-10 |
| DE1617521C3 (de) | 1979-09-06 |
| DE1617521B2 (de) | 1979-01-04 |
| ES340262A1 (es) | 1968-06-01 |
| IT1143624B (it) | 1986-10-22 |
| GB1176395A (en) | 1970-01-01 |
| DE1617521A1 (de) | 1972-02-10 |
| JPS5017524B1 (cg-RX-API-DMAC7.html) | 1975-06-21 |
| BE698102A (cg-RX-API-DMAC7.html) | 1967-11-08 |
| IL27876A (en) | 1971-10-20 |
| FR1523606A (fr) | 1968-05-03 |
| US3551564A (en) | 1970-12-29 |
| NL6706474A (cg-RX-API-DMAC7.html) | 1967-11-10 |
| DK117520B (da) | 1970-05-04 |
| NL140736B (nl) | 1974-01-15 |
| GR35814B (el) | 1968-11-04 |
| FI48975B (cg-RX-API-DMAC7.html) | 1974-12-02 |
| NO127486B (cg-RX-API-DMAC7.html) | 1973-07-02 |
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