PL73468B2 - - Google Patents
Download PDFInfo
- Publication number
- PL73468B2 PL73468B2 PL15623172A PL15623172A PL73468B2 PL 73468 B2 PL73468 B2 PL 73468B2 PL 15623172 A PL15623172 A PL 15623172A PL 15623172 A PL15623172 A PL 15623172A PL 73468 B2 PL73468 B2 PL 73468B2
- Authority
- PL
- Poland
- Prior art keywords
- general formula
- diazachalcone
- hydrazine
- derivative
- pyrazoline
- Prior art date
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims description 6
- FDFQUMOPQLALMR-UHFFFAOYSA-N 1-phenyl-3-pyridazin-3-ylprop-2-en-1-one Chemical compound C=1C=CC=CC=1C(=O)C=CC1=CC=CN=N1 FDFQUMOPQLALMR-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- 239000012024 dehydrating agents Substances 0.000 claims description 4
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 3
- 229940067157 phenylhydrazine Drugs 0.000 claims description 3
- 150000003219 pyrazolines Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- -1 1-phenyl-3,5-bis (3-pyridyl) -pyrazoline Chemical compound 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- YDGNZIFIIZJSSI-UHFFFAOYSA-N N1=CC=C(C=C1)N1NC=CC1 Chemical compound N1=CC=C(C=C1)N1NC=CC1 YDGNZIFIIZJSSI-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL15623172A PL73468B2 (enExample) | 1972-06-24 | 1972-06-24 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL15623172A PL73468B2 (enExample) | 1972-06-24 | 1972-06-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL73468B2 true PL73468B2 (enExample) | 1974-08-31 |
Family
ID=19959073
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL15623172A PL73468B2 (enExample) | 1972-06-24 | 1972-06-24 |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL73468B2 (enExample) |
-
1972
- 1972-06-24 PL PL15623172A patent/PL73468B2/pl unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Bower et al. | 907. Heterocyclic systems related to pyrrocoline. Part II. The preparation of polyazaindenes by dehydrogenative cyclisations | |
| JPS5843956A (ja) | Ｎ−（１，１，１−三置換）−メチルアゾ−ルの製造方法 | |
| JPS6396174A (ja) | 新規５−アルキルベンゾイミダゾール、その製法及び該化合物を含有する循環器系疾患治療剤 | |
| DE69202120T2 (de) | Harnstoffderivate, ihre Herstellung und ihre Verwendung bei der Therapie. | |
| KR100591935B1 (ko) | Ｎｍｄａ-수용체 아형 차단제로서의 피리딘 유도체 | |
| Geisler et al. | Synthesis of 1, 3-selenazoles and bis (selenazoles) from primary selenocarboxylic amides and selenourea | |
| DE69711081T2 (de) | Farnesyl transferase inhibitoren | |
| US3201406A (en) | Pyridylcoumarins | |
| PL73468B2 (enExample) | ||
| Kukolja et al. | Studies on· 4-Pyrones and 4-Pyridones. II. The Preparation. and Rearrangement of 3-Allyloxy-4-pyrone | |
| Anderson et al. | The reactions of 2-alkynylbenzaldehydes with hydrazides: a route to isoquinoline N-imines | |
| US3156697A (en) | Pyridylcoumarins | |
| Györgydeák et al. | Guanylhydrazones of (hetero) aryl methyl ketones: Structure and reaction with acetic anhydride | |
| Reddy et al. | 2‐Arylethenyl‐2′‐arylethynyl sulfones: A potential source for some spiroheterocycles | |
| US3435064A (en) | Process to convert activated methylene groups to the corresponding carbonyl groups | |
| Hegde et al. | Polyaza cavity shaped molecules 13. A versatile new terpyridine synthesis | |
| Sammes et al. | The reaction between 4-methoxy-2, 6-dimethylpyrylium perchlorate and amines. Isolation of both 4-iminiopyran salts and pyridinium salts in the reaction with primary amines | |
| Harutyunyan et al. | One‐pot effective synthesis of new heterocyclic system: Pyrano [4′, 3′: 4, 5] pyrido [2, 3‐d] pyrimidin‐6‐one | |
| US2389147A (en) | 4' methoxy 5 halogeno diphenylamino 2' carboxyl compound and process for producing the same | |
| Hassaneen et al. | Synthesis of some triazole, tetrazole, and tetrazine derivatives from N‐β‐naphthalenesulfonylbenzohydrazidoyl chlorides | |
| Sheradsky et al. | 2-Aminoarylation of heterocycles via a benzidine-like rearrangement | |
| US3329677A (en) | N-benzhydryloxyphthalimides and pryidinealdehyde o-benzhydryloximes | |
| Gohil et al. | Synthesis of Substituted 1, 2, 4-Triazole Containing Novel Small Molecules by Using Microwave | |
| Boyd et al. | The action of cyanamide on 1, 3, 4-oxadiazolium and pyrylium salts | |
| EP0189004A2 (de) | Verfahren zur Herstellung bestimmter in 3-Stellung substituierter Indole und Zwischenprodukte dafür |