ES416167A1 - 3-amino-pyrazolones-5, processes for their manufacture and their use as medicines - Google Patents
3-amino-pyrazolones-5, processes for their manufacture and their use as medicinesInfo
- Publication number
- ES416167A1 ES416167A1 ES416167A ES416167A ES416167A1 ES 416167 A1 ES416167 A1 ES 416167A1 ES 416167 A ES416167 A ES 416167A ES 416167 A ES416167 A ES 416167A ES 416167 A1 ES416167 A1 ES 416167A1
- Authority
- ES
- Spain
- Prior art keywords
- group
- alkyl
- phenyl
- formula
- alkoxy
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 229940079593 drug Drugs 0.000 title 1
- 239000003814 drug Substances 0.000 title 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 5
- 125000003545 alkoxy group Chemical group 0.000 abstract 5
- -1 carbonamido Chemical group 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000001424 substituent group Chemical group 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 abstract 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 150000001411 amidrazones Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 150000002429 hydrazines Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 150000004679 hydroxides Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 150000003460 sulfonic acids Chemical class 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 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
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/52—Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Procedure for the production of 3-aminopyrazolones- (5), of the formula **(See formula)** in which R represents a phenyl radical substituted by 1 to 2 substituents equal or different from the group consisting of alkyl, phenyl, trifluoromethoxy, nitro, cyano, carbonamido, sulfonamido, alkylamino, fluorine, bromine and iodine, with two substituents on the ring being Phenyl together eventually form a 5- to 7-membered saturated or unsaturated branched or unbranched isocyclic or heterocyclic ring capable of containing oxygen and/or sulfur atoms; or a phenyl radical substituted by a SOn-alkyl group (n = 0 to 2), an alkoxy group or the group -O- (CH2) n-N- (alkyl) 2 (n = 2 to 3); or a phenyl radical substituted by two equal substituents from the group consisting of alkoxy and trifluoromethyl; or a phenyl radical substituted by two different substituents from the group consisting of alkyl, phenyl, halogen, alkoxy, trifluoromethyl, trifluoromethoxy, alkylamino, cyano, carbonamido, sulfonamido, SOn-alkyl (n = 0 to 2) and nitro; or a phenyl radical substituted by three chlorine atoms; or a naphthyl radical substituted by 1 to 2 the same or different halogen atoms and/or alkyl, or an unsubstituted β-naphthyl, anthryl or phenanthril radical; characterized in that hydrazines of formula (II) are reacted R-CH2-NH-NH2 (II) in which R has the meaning defined above, with derivatives of acetic acid of formula (III) **(See formula)** where X is a hydroxy, alkoxy, aralkoxy, amino or alkylamino radical, Y'is hydrogen and Y''is nitrile or Y' and Y'' together represent the group **(See formula)** Y representing an alkoxy, aryloxy, aralkoxy, alkylmercapto or aralkylmercapto radical or the amino group, optionally after isolation of the intermediate amidrazones formed of the formula (IV) **(See formula)** in which X and R have the meanings indicated above, possibly in the presence of inert solvents and of basic or acid catalysts, such as alkali and alkaline earth hydroxides and carbonates or such as hydrohalic acids, sulfuric acid or sulfonic acids, at temperatures between 20º and 100ºC. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2230792A DE2230792A1 (en) | 1972-06-23 | 1972-06-23 | 3-AMINO-PYRAZOLONE- (5), METHOD FOR MANUFACTURING AND USING IT AS A MEDICINAL PRODUCT |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES416167A1 true ES416167A1 (en) | 1976-03-01 |
Family
ID=5848604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES416167A Expired ES416167A1 (en) | 1972-06-23 | 1973-06-22 | 3-amino-pyrazolones-5, processes for their manufacture and their use as medicines |
Country Status (29)
| Country | Link |
|---|---|
| JP (1) | JPS4962463A (en) |
| KR (1) | KR780000147B1 (en) |
| AR (1) | AR205329A1 (en) |
| AT (1) | AT323735B (en) |
| BE (1) | BE801228A (en) |
| BG (1) | BG22819A3 (en) |
| CA (1) | CA1017752A (en) |
| CH (1) | CH592632A5 (en) |
| DD (1) | DD109874A5 (en) |
| DE (1) | DE2230792A1 (en) |
| DK (1) | DK133468C (en) |
| EG (1) | EG11039A (en) |
| ES (1) | ES416167A1 (en) |
| FR (1) | FR2189072B1 (en) |
| GB (1) | GB1391051A (en) |
| HK (1) | HK11276A (en) |
| HU (1) | HU168358B (en) |
| IE (1) | IE37834B1 (en) |
| IL (1) | IL42560A (en) |
| LU (1) | LU67854A1 (en) |
| NL (1) | NL7308575A (en) |
| NO (1) | NO137196C (en) |
| OA (1) | OA04432A (en) |
| PH (1) | PH11606A (en) |
| PL (1) | PL87665B1 (en) |
| RO (1) | RO71819A (en) |
| SE (1) | SE401181B (en) |
| SU (1) | SU472503A3 (en) |
| ZA (1) | ZA734244B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE30420E (en) * | 1973-04-17 | 1980-10-21 | Bayer Aktiengesellschaft | Pyrazol-5-ones |
| DE2319278C2 (en) * | 1973-04-17 | 1986-02-20 | Bayer Ag, 5090 Leverkusen | Pharmaceutical agent |
| DE3436383A1 (en) * | 1984-10-04 | 1986-04-10 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING PYRAZOLONE DERIVATIVES |
-
1972
- 1972-06-23 DE DE2230792A patent/DE2230792A1/en not_active Withdrawn
-
1973
- 1973-06-06 RO RO7375048A patent/RO71819A/en unknown
- 1973-06-19 BG BG023919A patent/BG22819A3/en unknown
- 1973-06-20 IL IL42560A patent/IL42560A/en unknown
- 1973-06-20 NL NL7308575A patent/NL7308575A/xx not_active Application Discontinuation
- 1973-06-20 SE SE7308721A patent/SE401181B/en unknown
- 1973-06-20 SU SU1938995A patent/SU472503A3/en active
- 1973-06-20 CH CH897973A patent/CH592632A5/xx not_active IP Right Cessation
- 1973-06-20 AT AT544673A patent/AT323735B/en not_active IP Right Cessation
- 1973-06-21 DD DD171728A patent/DD109874A5/xx unknown
- 1973-06-21 EG EG235/73A patent/EG11039A/en active
- 1973-06-21 JP JP48069262A patent/JPS4962463A/ja active Pending
- 1973-06-21 LU LU67854A patent/LU67854A1/xx unknown
- 1973-06-21 BE BE132533A patent/BE801228A/en unknown
- 1973-06-22 AR AR248701A patent/AR205329A1/en active
- 1973-06-22 OA OA54946A patent/OA04432A/en unknown
- 1973-06-22 ZA ZA734244A patent/ZA734244B/en unknown
- 1973-06-22 GB GB2978573A patent/GB1391051A/en not_active Expired
- 1973-06-22 NO NO2618/73A patent/NO137196C/en unknown
- 1973-06-22 IE IE1035/73A patent/IE37834B1/en unknown
- 1973-06-22 HU HUBA2942A patent/HU168358B/hu unknown
- 1973-06-22 DK DK349573A patent/DK133468C/en active
- 1973-06-22 CA CA174,778A patent/CA1017752A/en not_active Expired
- 1973-06-22 FR FR7322955A patent/FR2189072B1/fr not_active Expired
- 1973-06-22 ES ES416167A patent/ES416167A1/en not_active Expired
- 1973-06-22 PL PL1973163511A patent/PL87665B1/pl unknown
- 1973-06-23 KR KR7301005A patent/KR780000147B1/en not_active Expired
-
1975
- 1975-01-03 PH PH16674A patent/PH11606A/en unknown
-
1976
- 1976-03-04 HK HK112/76*UA patent/HK11276A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2189072A1 (en) | 1974-01-25 |
| GB1391051A (en) | 1975-04-16 |
| CA1017752A (en) | 1977-09-20 |
| DK133468B (en) | 1976-05-24 |
| AU5705173A (en) | 1974-12-19 |
| IL42560A (en) | 1977-05-31 |
| HK11276A (en) | 1976-03-12 |
| EG11039A (en) | 1977-01-31 |
| CH592632A5 (en) | 1977-10-31 |
| IE37834L (en) | 1973-12-23 |
| OA04432A (en) | 1980-03-15 |
| SU472503A3 (en) | 1975-05-30 |
| SE401181B (en) | 1978-04-24 |
| BE801228A (en) | 1973-12-21 |
| NL7308575A (en) | 1973-12-27 |
| NO137196B (en) | 1977-10-10 |
| PH11606A (en) | 1978-04-12 |
| KR780000147B1 (en) | 1978-04-19 |
| LU67854A1 (en) | 1973-08-30 |
| JPS4962463A (en) | 1974-06-17 |
| DE2230792A1 (en) | 1974-01-17 |
| FR2189072B1 (en) | 1977-09-09 |
| ZA734244B (en) | 1974-06-26 |
| BG22819A3 (en) | 1977-04-20 |
| IE37834B1 (en) | 1977-10-26 |
| PL87665B1 (en) | 1976-07-31 |
| IL42560A0 (en) | 1973-08-29 |
| AR205329A1 (en) | 1976-04-30 |
| HU168358B (en) | 1976-04-28 |
| DD109874A5 (en) | 1974-11-20 |
| DK133468C (en) | 1976-10-18 |
| RO71819A (en) | 1981-01-30 |
| AT323735B (en) | 1975-07-25 |
| NO137196C (en) | 1978-01-18 |
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