DE2219763A1 - Pyrazolverbindungen. Ausscheidung aus: 2205136 - Google Patents
Pyrazolverbindungen. Ausscheidung aus: 2205136Info
- Publication number
- DE2219763A1 DE2219763A1 DE19722219763 DE2219763A DE2219763A1 DE 2219763 A1 DE2219763 A1 DE 2219763A1 DE 19722219763 DE19722219763 DE 19722219763 DE 2219763 A DE2219763 A DE 2219763A DE 2219763 A1 DE2219763 A1 DE 2219763A1
- Authority
- DE
- Germany
- Prior art keywords
- mol
- elimination
- pyrazole compounds
- div
- compounds
- 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
- 150000003217 pyrazoles Chemical class 0.000 title description 3
- 230000008030 elimination Effects 0.000 title 1
- 238000003379 elimination reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
- 229940075930 picrate Drugs 0.000 description 4
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- -1 η-butyl Chemical group 0.000 description 3
- ZFDGMMZLXSFNFU-UHFFFAOYSA-N 2,5-dimethylpyrazol-3-amine Chemical compound CC=1C=C(N)N(C)N=1 ZFDGMMZLXSFNFU-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- UCXPESOPEKJXJR-UHFFFAOYSA-N 1,2-bis(4-chlorophenyl)-2-hydroxyethanone Chemical compound C=1C=C(Cl)C=CC=1C(O)C(=O)C1=CC=C(Cl)C=C1 UCXPESOPEKJXJR-UHFFFAOYSA-N 0.000 description 1
- RNAMYOYQYRYFQY-UHFFFAOYSA-N 2-(4,4-difluoropiperidin-1-yl)-6-methoxy-n-(1-propan-2-ylpiperidin-4-yl)-7-(3-pyrrolidin-1-ylpropoxy)quinazolin-4-amine Chemical compound N1=C(N2CCC(F)(F)CC2)N=C2C=C(OCCCN3CCCC3)C(OC)=CC2=C1NC1CCN(C(C)C)CC1 RNAMYOYQYRYFQY-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 229940125716 antipyretic agent Drugs 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D231/38—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Luminescent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11276771A | 1971-02-04 | 1971-02-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2219763A1 true DE2219763A1 (de) | 1972-12-28 |
Family
ID=22345736
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722219763 Pending DE2219763A1 (de) | 1971-02-04 | 1972-02-03 | Pyrazolverbindungen. Ausscheidung aus: 2205136 |
| DE19722205136 Pending DE2205136A1 (de) | 1971-02-04 | 1972-02-03 | l,3-Dimethyl-4,5-di-(p-substit.-phenyl)-6H-pyrrolo eckige Klammer auf 2,3-c eckige Klammer zu pyrazole |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722205136 Pending DE2205136A1 (de) | 1971-02-04 | 1972-02-03 | l,3-Dimethyl-4,5-di-(p-substit.-phenyl)-6H-pyrrolo eckige Klammer auf 2,3-c eckige Klammer zu pyrazole |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3701785A (enExample) |
| AU (1) | AU460296B2 (enExample) |
| CA (1) | CA987673A (enExample) |
| CH (1) | CH550789A (enExample) |
| DE (2) | DE2219763A1 (enExample) |
| FR (1) | FR2124450B1 (enExample) |
| GB (1) | GB1333351A (enExample) |
| ZA (1) | ZA72148B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3867402A (en) * | 1973-03-15 | 1975-02-18 | Abbott Lab | 1-methyl-4,5-di(p-methoxyphenyl)-6h-pyrrolo(2,3-c) pyrazole |
-
1971
- 1971-01-10 ZA ZA720148A patent/ZA72148B/xx unknown
- 1971-02-04 US US112767A patent/US3701785A/en not_active Expired - Lifetime
-
1972
- 1972-01-06 CA CA131,807A patent/CA987673A/en not_active Expired
- 1972-01-13 AU AU37896/72A patent/AU460296B2/en not_active Expired
- 1972-01-14 GB GB196572A patent/GB1333351A/en not_active Expired
- 1972-02-03 DE DE19722219763 patent/DE2219763A1/de active Pending
- 1972-02-03 DE DE19722205136 patent/DE2205136A1/de active Pending
- 1972-02-03 FR FR7203667A patent/FR2124450B1/fr not_active Expired
- 1972-02-04 CH CH163772A patent/CH550789A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1333351A (en) | 1973-10-10 |
| CA987673A (en) | 1976-04-20 |
| FR2124450A1 (enExample) | 1972-09-22 |
| CH550789A (fr) | 1974-06-28 |
| US3701785A (en) | 1972-10-31 |
| FR2124450B1 (enExample) | 1974-11-15 |
| DE2205136A1 (de) | 1972-08-17 |
| AU460296B2 (en) | 1975-04-24 |
| AU3789672A (en) | 1973-07-19 |
| ZA72148B (en) | 1972-09-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2365852B2 (de) | Verfahren zur Herstellung von Monoacetalen aromatischer 1,2-Diketone | |
| DE2219763A1 (de) | Pyrazolverbindungen. Ausscheidung aus: 2205136 | |
| DE1227914B (de) | Verfahren zur Herstellung von 3-(1, 2-Dithia-cyclopentyl)-5-pentansaeure | |
| DE1793693C3 (enExample) | ||
| DE1670920A1 (de) | N-Disubstituierte 3-Amino-1,2-benzisothiazol-Derivate | |
| AT228785B (de) | Verfahren zur Herstellung neuer basisch substituierter Triphenylcarbinole und deren Salze | |
| DE2063502C3 (de) | Verfahren zur Herstellung von Aminocarbonsäure-Vorstufen | |
| DE1914496C3 (de) | Verfahren zur Herstellung von 1,2,5 -Thiadiazolderivaten | |
| DE822552C (de) | Verfahren zur Herstellung von Alkylderivaten von Diketooxazolidinen | |
| DE935433C (de) | Verfahren zur Herstellung von Glycidestern von Sulfonsaeuren | |
| AT203496B (de) | Verfahren zur Herstellung von neuen tertiären Aminen | |
| AT308085B (de) | Verfahren zum Herstellen von neuen Derivaten des Äthylendiamins | |
| DE2660902C2 (de) | Dicarbonsäure-bis[3,5-bis(chlorcarbonyl)-2,4,6-trijodanilid]- Verbindungen und deren Herstellung | |
| AT227678B (de) | Verfahren zur Herstellung von neuen Sulfensäure-Derivaten | |
| DE1056132B (de) | Verfahren zur Herstellung von Thionothiolphosphorsaeureestern | |
| DE870121C (de) | Verfahren zur Herstellung von Aminen | |
| AT283361B (de) | Verfahren zur herstellung neuer zimtsaeureamide | |
| AT256825B (de) | Verfahren zur Herstellung von neuen heterocyclischen Benzamidoverbindungen und ihren Salzen | |
| DE1542826C (de) | Sulfoniumverbindungen und deren Verwendung | |
| DE1026323B (de) | Verfahren zur Herstellung von insekticid wirksamen O, O-Dialkyl-S-phenyl-thionothiolphosphorsaeureestern | |
| DE1593783A1 (de) | Verfahren zur Herstellung von 1-(2-Nitrilophenoxy)-2-hydroxy-3-isopropylaminopropan und dessen Salzen | |
| DE3142654A1 (de) | "verfahren zur herstellung von triiod-vinyl-verbindungen" | |
| DE1104955B (de) | Verfahren zur Herstellung von substituierten Fulvenaldehyden | |
| CH373389A (de) | Verfahren zur Herstellung von neuen Azetidin-Derivaten | |
| DE1618863A1 (de) | Verfahren zur Herstellung neuer 3-Alkoxycarbonyl-2-phenyl-1,3-butadien-Derivate |