DD154817A5 - Verfahren zur darstellung der molekularen verbindung von beta-diaethylaminoaethylamid der p-chlorophenoxyessigsaeure mit 4-n-butyl-3,5-diketo-1,2-diphenylpyrazolidin - Google Patents
Verfahren zur darstellung der molekularen verbindung von beta-diaethylaminoaethylamid der p-chlorophenoxyessigsaeure mit 4-n-butyl-3,5-diketo-1,2-diphenylpyrazolidin Download PDFInfo
- Publication number
- DD154817A5 DD154817A5 DD80225497A DD22549780A DD154817A5 DD 154817 A5 DD154817 A5 DD 154817A5 DD 80225497 A DD80225497 A DD 80225497A DD 22549780 A DD22549780 A DD 22549780A DD 154817 A5 DD154817 A5 DD 154817A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- butyl
- diketo
- molecular compound
- diphenylpyrazolidine
- beta
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims abstract description 14
- 239000002253 acid Substances 0.000 title 1
- SODPIMGUZLOIPE-UHFFFAOYSA-N (4-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1 SODPIMGUZLOIPE-UHFFFAOYSA-N 0.000 claims abstract description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 239000012454 non-polar solvent Substances 0.000 claims abstract description 4
- 239000002798 polar solvent Substances 0.000 claims abstract description 4
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 claims description 18
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 10
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 claims description 2
- -1 4-n-butyl Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000002260 anti-inflammatory agent Substances 0.000 abstract description 3
- 229940124599 anti-inflammatory drug Drugs 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 238000009835 boiling Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 238000007112 amidation reaction Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000009435 amidation Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- IRMCWHUVXQCWKI-UHFFFAOYSA-N 1,2-diphenylpyrazolidine Chemical compound C1CCN(C=2C=CC=CC=2)N1C1=CC=CC=C1 IRMCWHUVXQCWKI-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000012320 chlorinating reagent Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XDPKQGKEOCYMQC-UHFFFAOYSA-N 1,2-diphenylpyrazolidine-3,5-dione Chemical compound O=C1CC(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 XDPKQGKEOCYMQC-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OOAZUBZKWZANJJ-UHFFFAOYSA-N 2-[(4-chlorophenoxy)methyl]-4,5-dihydro-1,3-oxazole Chemical compound C1=CC(Cl)=CC=C1OCC1=NCCO1 OOAZUBZKWZANJJ-UHFFFAOYSA-N 0.000 description 1
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000011938 amidation process Methods 0.000 description 1
- 230000001741 anti-phlogistic effect Effects 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/28—Two oxygen or sulfur atoms
- C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
- C07D231/32—Oxygen atoms
- C07D231/34—Oxygen atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (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 |
|---|---|---|---|
| PL1979219874A PL122256B1 (en) | 1979-11-26 | 1979-11-26 | Process for preparing molecular compound of beta-diethylaminoethylamide of p-chlorophenoxyacetic acid with 4-n-butyl-3,5-diketo-1,2-diphenylpyrazolidin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD154817A5 true DD154817A5 (de) | 1982-04-21 |
Family
ID=19999619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80225497A DD154817A5 (de) | 1979-11-26 | 1980-11-26 | Verfahren zur darstellung der molekularen verbindung von beta-diaethylaminoaethylamid der p-chlorophenoxyessigsaeure mit 4-n-butyl-3,5-diketo-1,2-diphenylpyrazolidin |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5687567A (cs) |
| CS (1) | CS212286B2 (cs) |
| DD (1) | DD154817A5 (cs) |
| GB (1) | GB2064522B (cs) |
| HU (1) | HU185287B (cs) |
| PL (1) | PL122256B1 (cs) |
| RO (1) | RO81174B (cs) |
| SU (1) | SU1034605A3 (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU203538B (en) * | 1988-03-10 | 1991-08-28 | Richter Gedeon Vegyeszet | Process for producing 1,2-diphenyl-3,5-dioxy-4-butyl-pirazolidin-sodium-monohydrate |
| IT1282693B1 (it) * | 1996-02-27 | 1998-03-31 | Dompe Spa | Acidi carbossilici geminali e loro esteri;preparazioni farmaceutiche che li contengono utili nel trattamento del dismetabolismo osseo |
| US11130729B2 (en) | 2017-06-13 | 2021-09-28 | Lapko Inc. | CCL2 inhibitors |
-
1979
- 1979-11-26 PL PL1979219874A patent/PL122256B1/pl unknown
-
1980
- 1980-11-12 SU SU803003653A patent/SU1034605A3/ru active
- 1980-11-12 GB GB8036306A patent/GB2064522B/en not_active Expired
- 1980-11-14 CS CS807738A patent/CS212286B2/cs unknown
- 1980-11-21 RO RO102656A patent/RO81174B/ro unknown
- 1980-11-25 JP JP16577880A patent/JPS5687567A/ja active Pending
- 1980-11-26 HU HU802826A patent/HU185287B/hu unknown
- 1980-11-26 DD DD80225497A patent/DD154817A5/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SU1034605A3 (ru) | 1983-08-07 |
| RO81174A (ro) | 1983-04-29 |
| PL122256B1 (en) | 1982-07-31 |
| PL219874A1 (cs) | 1981-06-05 |
| GB2064522B (en) | 1983-05-11 |
| JPS5687567A (en) | 1981-07-16 |
| HU185287B (en) | 1984-12-28 |
| RO81174B (ro) | 1983-04-30 |
| GB2064522A (en) | 1981-06-17 |
| CS212286B2 (en) | 1982-03-26 |
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