DE1593112C3 - o-Hydroxybenzoyl-hydrazon oder o-Alkyloxy-benzoyl-hydrazone der Brenztraubensäure und Verfahren zu deren Herstellung - Google Patents
o-Hydroxybenzoyl-hydrazon oder o-Alkyloxy-benzoyl-hydrazone der Brenztraubensäure und Verfahren zu deren HerstellungInfo
- Publication number
- DE1593112C3 DE1593112C3 DE1593112A DE1593112A DE1593112C3 DE 1593112 C3 DE1593112 C3 DE 1593112C3 DE 1593112 A DE1593112 A DE 1593112A DE 1593112 A DE1593112 A DE 1593112A DE 1593112 C3 DE1593112 C3 DE 1593112C3
- Authority
- DE
- Germany
- Prior art keywords
- hydrazone
- pyruvic acid
- benzoyl
- hydroxybenzoyl
- 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
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 title claims description 28
- 229940107700 pyruvic acid Drugs 0.000 title claims description 14
- 238000000034 method Methods 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 3
- -1 o-Hydroxybenzoyl hydrazone Chemical class 0.000 claims description 6
- 150000007857 hydrazones Chemical class 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 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 3
- 206010030113 Oedema Diseases 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 2
- 241000206575 Chondrus crispus Species 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 2
- ACONNXZOJIHEHN-UHFFFAOYSA-N 2-[(2-ethoxybenzoyl)hydrazinylidene]propanoic acid Chemical compound CCOC1=CC=CC=C1C(=O)NN=C(C)C(O)=O ACONNXZOJIHEHN-UHFFFAOYSA-N 0.000 description 1
- XDZMPRGFOOFSBL-UHFFFAOYSA-N 2-ethoxybenzoic acid Chemical compound CCOC1=CC=CC=C1C(O)=O XDZMPRGFOOFSBL-UHFFFAOYSA-N 0.000 description 1
- RXXLWJKVDZLVHR-UHFFFAOYSA-N 4-benzyl-5-methylpyrazol-3-one Chemical compound O=C1N=NC(C)=C1CC1=CC=CC=C1 RXXLWJKVDZLVHR-UHFFFAOYSA-N 0.000 description 1
- QDPFZXUJYAPGKK-UHFFFAOYSA-N CNCS(=O)(=O)O.C1(=CC=CC=C1)CC=1C(N=NC1C)=O Chemical compound CNCS(=O)(=O)O.C1(=CC=CC=C1)CC=1C(N=NC1C)=O QDPFZXUJYAPGKK-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 230000003356 anti-rheumatic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2634465 | 1965-11-23 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1593112A1 DE1593112A1 (de) | 1970-07-16 |
| DE1593112B2 DE1593112B2 (de) | 1973-10-25 |
| DE1593112C3 true DE1593112C3 (de) | 1974-05-30 |
Family
ID=11219271
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1593112A Expired DE1593112C3 (de) | 1965-11-23 | 1966-11-18 | o-Hydroxybenzoyl-hydrazon oder o-Alkyloxy-benzoyl-hydrazone der Brenztraubensäure und Verfahren zu deren Herstellung |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3651133A (OSRAM) |
| AT (1) | AT266074B (OSRAM) |
| BE (1) | BE689985A (OSRAM) |
| CH (1) | CH482651A (OSRAM) |
| DE (1) | DE1593112C3 (OSRAM) |
| FR (2) | FR1501437A (OSRAM) |
| GB (1) | GB1133647A (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1768137A1 (de) * | 1968-04-04 | 1971-11-18 | Hoechst Ag | Substituierte p-Hydroxyphenylhydrazone und Verfahren zu ihrer Herstellung |
| NL6904480A (OSRAM) * | 1968-04-04 | 1969-10-07 | ||
| DE1768135A1 (de) * | 1968-04-04 | 1971-10-07 | Hoechst Ag | Substituierte p-Hydroxyphenylhydrazone und Verfahren zu ihrer Herstellung |
| DE1768136A1 (de) * | 1968-04-04 | 1971-10-14 | Hoechst Ag | Substituierte p-Hydrophenylhydrazone und Verfahren zu ihrer Herstellung |
| GB1418595A (en) * | 1973-02-14 | 1975-12-24 | Ss Pharmaceutical Co | N- 2-alkoxybenzoyl- amino acids and a process for producing the same |
-
1966
- 1966-11-15 GB GB51050/66A patent/GB1133647A/en not_active Expired
- 1966-11-18 DE DE1593112A patent/DE1593112C3/de not_active Expired
- 1966-11-21 BE BE689985D patent/BE689985A/xx unknown
- 1966-11-22 US US596092A patent/US3651133A/en not_active Expired - Lifetime
- 1966-11-22 FR FR84496A patent/FR1501437A/fr not_active Expired
- 1966-11-23 CH CH1701266A patent/CH482651A/fr not_active IP Right Cessation
- 1966-11-23 AT AT1082766A patent/AT266074B/de active
-
1967
- 1967-02-22 FR FR96035A patent/FR6232M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT266074B (de) | 1968-11-11 |
| FR1501437A (fr) | 1967-11-10 |
| FR6232M (OSRAM) | 1968-08-05 |
| CH482651A (fr) | 1969-12-15 |
| DE1593112B2 (de) | 1973-10-25 |
| DE1593112A1 (de) | 1970-07-16 |
| US3651133A (en) | 1972-03-21 |
| BE689985A (OSRAM) | 1967-05-02 |
| GB1133647A (en) | 1968-11-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |