DE2925345C2 - N[β-(2-Mercaptoäthylcarbamoyl)-äthyl]-phenoxyalkansäureamide, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zubereitungen - Google Patents
N[β-(2-Mercaptoäthylcarbamoyl)-äthyl]-phenoxyalkansäureamide, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische ZubereitungenInfo
- Publication number
- DE2925345C2 DE2925345C2 DE2925345A DE2925345A DE2925345C2 DE 2925345 C2 DE2925345 C2 DE 2925345C2 DE 2925345 A DE2925345 A DE 2925345A DE 2925345 A DE2925345 A DE 2925345A DE 2925345 C2 DE2925345 C2 DE 2925345C2
- Authority
- DE
- Germany
- Prior art keywords
- ethyl
- mercaptoethylcarbamoyl
- compounds
- processes
- preparation
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title description 11
- -1 2-mercaptoethylcarbamoyl Chemical group 0.000 title description 4
- 238000000034 method Methods 0.000 title description 4
- 239000000825 pharmaceutical preparation Substances 0.000 title description 2
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001408 amides Chemical class 0.000 title 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- 241001494479 Pecora Species 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 229960001614 levamisole Drugs 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 210000003743 erythrocyte Anatomy 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 230000003308 immunostimulating effect Effects 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 210000004989 spleen cell Anatomy 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000005875 antibody response Effects 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 2
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- QYOZUXBNKMDZDK-UHFFFAOYSA-N 2-(3,5-ditert-butylphenoxy)-2-methylpropanamide;propanenitrile Chemical compound CCC#N.CC(C)(C)C1=CC(OC(C)(C)C(N)=O)=CC(C(C)(C)C)=C1 QYOZUXBNKMDZDK-UHFFFAOYSA-N 0.000 description 1
- NWXPFHLRADFKRL-UHFFFAOYSA-N 2-(4-chlorophenoxy)-2-methylpropanamide Chemical compound NC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 NWXPFHLRADFKRL-UHFFFAOYSA-N 0.000 description 1
- ZDWSNKPLZUXBPE-UHFFFAOYSA-N 3,5-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(O)=CC(C(C)(C)C)=C1 ZDWSNKPLZUXBPE-UHFFFAOYSA-N 0.000 description 1
- 108010042708 Acetylmuramyl-Alanyl-Isoglutamine Proteins 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 241000607734 Yersinia <bacteria> Species 0.000 description 1
- WBLXMRIMSGHSAC-UHFFFAOYSA-N [Cl].[Cl] Chemical compound [Cl].[Cl] WBLXMRIMSGHSAC-UHFFFAOYSA-N 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229960003151 mercaptamine Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- BSOQXXWZTUDTEL-ZUYCGGNHSA-N muramyl dipeptide Chemical compound OC(=O)CC[C@H](C(N)=O)NC(=O)[C@H](C)NC(=O)[C@@H](C)O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](O)[C@@H]1NC(C)=O BSOQXXWZTUDTEL-ZUYCGGNHSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011268 retreatment Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPD482178 | 1978-06-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2925345A1 DE2925345A1 (de) | 1980-01-10 |
| DE2925345C2 true DE2925345C2 (de) | 1984-04-19 |
Family
ID=3767615
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2925345A Expired DE2925345C2 (de) | 1978-06-22 | 1979-06-22 | N[β-(2-Mercaptoäthylcarbamoyl)-äthyl]-phenoxyalkansäureamide, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zubereitungen |
Country Status (23)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4552765A (en) * | 1982-05-14 | 1985-11-12 | Santen Pharmaceutical Co., Ltd. | Aletheine derivatives |
| WO1997014306A1 (en) * | 1995-10-17 | 1997-04-24 | Dovetail Technologies, Inc. | Low molecular weight cell, bone marrow and immune stimulants |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1185180B (de) * | 1963-10-19 | 1965-01-14 | Hoechst Ag | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
| DE2622977C2 (de) * | 1976-05-21 | 1985-04-11 | Kotobuki Seiyaku Co. Ltd., Nagano | p-Chlorphenoxyisobutyryl-glycinamid, Verfahren zu dessen Herstellung und diese Verbindung enthaltendes, den Fettstoffwechsel förderndes Mittel |
-
1978
- 1978-06-22 AU AU47879/79A patent/AU528362B2/en not_active Ceased
-
1979
- 1979-05-22 IN IN360/DEL/79A patent/IN152133B/en unknown
- 1979-05-23 ZA ZA792513A patent/ZA792513B/xx unknown
- 1979-05-28 NZ NZ190563A patent/NZ190563A/xx unknown
- 1979-05-30 BE BE0/195467A patent/BE876643A/xx not_active IP Right Cessation
- 1979-05-30 GB GB7918779A patent/GB2023592B/en not_active Expired
- 1979-06-01 LU LU81355A patent/LU81355A1/xx unknown
- 1979-06-11 AT AT0415779A patent/AT365560B/de not_active IP Right Cessation
- 1979-06-14 NL NL7904657A patent/NL7904657A/xx not_active Application Discontinuation
- 1979-06-18 PT PT69770A patent/PT69770A/pt unknown
- 1979-06-18 CH CH565779A patent/CH638182A5/fr not_active IP Right Cessation
- 1979-06-19 ES ES481669A patent/ES481669A1/es not_active Expired
- 1979-06-19 US US06/050,106 patent/US4256767A/en not_active Expired - Lifetime
- 1979-06-20 SE SE7905432A patent/SE7905432L/xx not_active Application Discontinuation
- 1979-06-21 DK DK260079A patent/DK260079A/da not_active Application Discontinuation
- 1979-06-22 FR FR7916022A patent/FR2429202B1/fr not_active Expired
- 1979-06-22 OA OA56833A patent/OA06280A/xx unknown
- 1979-06-22 JP JP7827979A patent/JPS557275A/ja active Granted
- 1979-06-22 FR FR7916021A patent/FR2429017B1/fr not_active Expired
- 1979-06-22 DE DE2925345A patent/DE2925345C2/de not_active Expired
- 1979-06-22 AR AR277003A patent/AR220205A1/es active
- 1979-06-22 CA CA000330642A patent/CA1116631A/en not_active Expired
-
1983
- 1983-10-13 HK HK426/83A patent/HK42683A/xx unknown
-
1984
- 1984-12-30 MY MY85/84A patent/MY8400085A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8125 | Change of the main classification |
Ipc: C07C103/50 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |