DE2242779A1 - Chlorphenesinderivate, verfahren zu ihrer herstellung und ihre verwendung als oder in einem arzneimittel - Google Patents
Chlorphenesinderivate, verfahren zu ihrer herstellung und ihre verwendung als oder in einem arzneimittelInfo
- Publication number
- DE2242779A1 DE2242779A1 DE2242779A DE2242779A DE2242779A1 DE 2242779 A1 DE2242779 A1 DE 2242779A1 DE 2242779 A DE2242779 A DE 2242779A DE 2242779 A DE2242779 A DE 2242779A DE 2242779 A1 DE2242779 A1 DE 2242779A1
- Authority
- DE
- Germany
- Prior art keywords
- chlorphenesin
- succinate
- alkali metal
- metal salts
- sodium
- 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
- 238000000034 method Methods 0.000 title claims description 13
- 229940126601 medicinal product Drugs 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 5
- MXOAEAUPQDYUQM-QMMMGPOBSA-N (S)-chlorphenesin Chemical compound OC[C@H](O)COC1=CC=C(Cl)C=C1 MXOAEAUPQDYUQM-QMMMGPOBSA-N 0.000 claims description 35
- 229960003993 chlorphenesin Drugs 0.000 claims description 30
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 22
- 229910052783 alkali metal Inorganic materials 0.000 claims description 15
- -1 alkali metal salts Chemical class 0.000 claims description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 229940014800 succinic anhydride Drugs 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000001632 sodium acetate Substances 0.000 claims description 3
- 235000017281 sodium acetate Nutrition 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229940072033 potash Drugs 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 1
- 235000015320 potassium carbonate Nutrition 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 12
- 239000013256 coordination polymer Substances 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229960001340 histamine Drugs 0.000 description 6
- MXOAEAUPQDYUQM-UHFFFAOYSA-N chlorphenesin Chemical compound OCC(O)COC1=CC=C(Cl)C=C1 MXOAEAUPQDYUQM-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000000427 antigen Substances 0.000 description 3
- 102000036639 antigens Human genes 0.000 description 3
- 108091007433 antigens Proteins 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 210000003630 histaminocyte Anatomy 0.000 description 3
- 210000000265 leukocyte Anatomy 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000700199 Cavia porcellus Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 230000003266 anti-allergic effect Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 210000003491 skin Anatomy 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 229930003347 Atropine Natural products 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 231100000369 acute toxicity data Toxicity 0.000 description 1
- 230000002052 anaphylactic effect Effects 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
- 229960000396 atropine Drugs 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 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
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005303 weighing Methods 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP46067494A JPS504650B2 (OSRAM) | 1971-09-03 | 1971-09-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2242779A1 true DE2242779A1 (de) | 1973-03-08 |
Family
ID=13346584
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2242779A Pending DE2242779A1 (de) | 1971-09-03 | 1972-08-31 | Chlorphenesinderivate, verfahren zu ihrer herstellung und ihre verwendung als oder in einem arzneimittel |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3846480A (OSRAM) |
| JP (1) | JPS504650B2 (OSRAM) |
| DE (1) | DE2242779A1 (OSRAM) |
| GB (1) | GB1394397A (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9201138D0 (sv) * | 1992-04-09 | 1992-04-09 | Astra Ab | Novel phthalimidoalkylpiperazines |
| AUPO983897A0 (en) | 1997-10-17 | 1997-11-06 | Soltec Research Pty Ltd | Topical antifungal composition |
| US6696048B2 (en) * | 2001-12-20 | 2004-02-24 | Schering-Plough Healthcare Products, Inc. | Sunscreen composition |
| CN119818469A (zh) * | 2025-01-08 | 2025-04-15 | 中国科学院长春应用化学研究所 | 一种琥珀酸盐纳米药物、其制备方法及应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2586661A (en) * | 1949-12-14 | 1952-02-19 | Rhone Poulenc Sa | Process for the resolution of an amino-diol racemate |
| US2663727A (en) * | 1950-10-28 | 1953-12-22 | Parke Davis & Co | Diastereoisomeric propane derivatives and process for their manufacture |
| US2988481A (en) * | 1958-05-02 | 1961-06-13 | Du Pont | Compositions of aliphatic dibasic acid half esters of dichloracetyl-phenylpropanediols |
-
1971
- 1971-09-03 JP JP46067494A patent/JPS504650B2/ja not_active Expired
-
1972
- 1972-08-28 US US00284357A patent/US3846480A/en not_active Expired - Lifetime
- 1972-08-31 DE DE2242779A patent/DE2242779A1/de active Pending
- 1972-09-04 GB GB4087572A patent/GB1394397A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4834135A (OSRAM) | 1973-05-16 |
| JPS504650B2 (OSRAM) | 1975-02-22 |
| US3846480A (en) | 1974-11-05 |
| GB1394397A (en) | 1975-05-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1518764C3 (de) | In der 7-Stellung substituierte S-Phenyl-2-oxo-23-dihydro-lH-1 ^-benzodiazepin-S-carbonsäuresalze und -alkylester | |
| DE2242779A1 (de) | Chlorphenesinderivate, verfahren zu ihrer herstellung und ihre verwendung als oder in einem arzneimittel | |
| CH460041A (de) | Verfahren zur Herstellung von 4-substituierten 4'-tert.-Aminoalkoxyphenylen | |
| DE2653218A1 (de) | Praeparate | |
| DE1770579A1 (de) | Verfahren zur Herstellung von Rifamycin | |
| DE3788693T2 (de) | 3,5-Dichloro-2,4-dimethoxy-6-(trichlormethyl)pyridine. | |
| DE1795731A1 (de) | Verfahren zur herstellung neuer antibiotisch wirksamer verbindungen | |
| DE2721766C2 (OSRAM) | ||
| DE2037171C3 (de) | 7-Methyl-8-styryIxanthine und Verfahren zu ihrer Herstellung | |
| DE1545782A1 (de) | Neue Noralkaloide und Verfahren zu deren Herstellung | |
| DE2164790A1 (de) | Flavanonderivate | |
| DE2241076B2 (de) | Tetracyclinkomplex und dessen Salze, Verfahren zu dessen Herstellung und diesen Komplex enthaltende pharmazeutische Zusammensetzungen | |
| DE1695832C3 (de) | B1,3-biphenylpyrazolin-Derivate und Verfahren zu ihrer Herstellung | |
| DE1670378A1 (de) | Verfahren zur Herstellung einer Verbindung aus Phenylbutazon und ss-Diaethylaminoaethylamid der p-Chlorphenoxyessigsaeure | |
| DE2413802A1 (de) | Gemischte salze von sulfoglykopeptiden mit metallbasen und organischen basen und verfahren zu ihrer herstellung | |
| DE2432322A1 (de) | Neues pyridinderivat und seine additionssalze, herstellungsverfahren dafuer sowie pharmazeutische zusammensetzungen | |
| DE1122514B (de) | Verfahren zur Herstellung von blutdrucksteigerndem 2-AEthyl-3,3-diphenyl-propen-(2)-yl-amin | |
| DE1617795C3 (OSRAM) | ||
| DE1445417A1 (de) | Verfahren zur Herstellung von neuen Hexitestern der Nikotinsaeure | |
| DE723698C (de) | Verfahren zur Gewinnung von wasser- und lipoidloeslichen Wirkstoffen aus tierischen oder pflanzlichen Organen | |
| AT159431B (de) | Verfahren zur Herstellung organischer Jodverbindungen. | |
| DE525403C (de) | Verfahren zur Darstellung von wasserloeslichen Kondensationsprodukten der Aminoarylarsinoxyde | |
| DE731561C (de) | Verfahren zur Herstellung von im stickstoffhaltigen Kern aralkylsubstituierten und in einem aromatischen Kern freie Hydroxylgruppen enthaltenden hydrierten Isochinolinverbindungen | |
| AT226883B (de) | Verfahren zur Herstellung von löslichen, kohlehydratfreien Lecithinverbindungen | |
| DE1543224A1 (de) | Dibenzocycloheptenderivate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |