SU522800A3 - Способ получени производных пиразоло (1,5-а) пиримидина - Google Patents
Способ получени производных пиразоло (1,5-а) пиримидинаInfo
- Publication number
- SU522800A3 SU522800A3 SU1821375A SU1821375A SU522800A3 SU 522800 A3 SU522800 A3 SU 522800A3 SU 1821375 A SU1821375 A SU 1821375A SU 1821375 A SU1821375 A SU 1821375A SU 522800 A3 SU522800 A3 SU 522800A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- solution
- sodium
- water
- acid
- product
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 18
- 159000000000 sodium salts Chemical class 0.000 claims description 15
- 229910052708 sodium Inorganic materials 0.000 claims description 13
- 239000011734 sodium Substances 0.000 claims description 13
- 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 claims description 12
- 238000001914 filtration Methods 0.000 claims description 11
- 238000010992 reflux Methods 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 8
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- -1 m-tolyl-pyrazolo (1.5-a) pyrimidine-7-ol Chemical compound 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 4
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 claims description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- ZRZFBIGKTXTOQY-UHFFFAOYSA-N OC1=CC=NC2=CC=NN12 Chemical compound OC1=CC=NC2=CC=NN12 ZRZFBIGKTXTOQY-UHFFFAOYSA-N 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229960005235 piperonyl butoxide Drugs 0.000 claims 1
- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims 1
- 150000003230 pyrimidines Chemical class 0.000 claims 1
- 239000000052 vinegar Substances 0.000 claims 1
- 235000021419 vinegar Nutrition 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
- 239000000047 product Substances 0.000 description 30
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 11
- 238000000354 decomposition reaction Methods 0.000 description 10
- 238000001556 precipitation Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 206010062717 Increased upper airway secretion Diseases 0.000 description 4
- 230000020477 pH reduction Effects 0.000 description 4
- 208000026435 phlegm Diseases 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- VAKJBMPZWKCBAW-UHFFFAOYSA-N 4-(3-methylphenyl)-1h-pyrazol-5-amine Chemical compound CC1=CC=CC(C2=C(NN=C2)N)=C1 VAKJBMPZWKCBAW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- CTZUARZJFPNNTM-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-ylmethyl)-1h-pyrazol-5-amine Chemical compound N1N=CC(CC=2C=C3OCOC3=CC=2)=C1N CTZUARZJFPNNTM-UHFFFAOYSA-N 0.000 description 1
- ABKUXQSVMWMABM-UHFFFAOYSA-N 4-(4-bromophenyl)-1h-pyrazol-5-amine Chemical compound N1N=CC(C=2C=CC(Br)=CC=2)=C1N ABKUXQSVMWMABM-UHFFFAOYSA-N 0.000 description 1
- QEHKQNYBBLCFIJ-UHFFFAOYSA-N 4-phenyl-1h-pyrazol-5-amine Chemical compound NC1=NNC=C1C1=CC=CC=C1 QEHKQNYBBLCFIJ-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- REHHBTUVMSHZNT-UHFFFAOYSA-N bromocyclohexatriene Chemical group BrC1=CC=C=C[CH]1 REHHBTUVMSHZNT-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- BKWUGUDGIFXDOX-UHFFFAOYSA-N chembl156470 Chemical compound C1=NN2C(O)=CC=NC2=C1C1=CC=CC=C1 BKWUGUDGIFXDOX-UHFFFAOYSA-N 0.000 description 1
- UMOILRYDPQMJET-UHFFFAOYSA-N chembl3276839 Chemical compound C=12N=C(O)C=C(O)N2N=CC=1C1=CC=CC=C1 UMOILRYDPQMJET-UHFFFAOYSA-N 0.000 description 1
- GSWVYYXDNVSEAU-UHFFFAOYSA-N chembl3276840 Chemical compound C=12N=C(O)C=C(O)N2N=CC=1C1=CC=CN=C1 GSWVYYXDNVSEAU-UHFFFAOYSA-N 0.000 description 1
- ROYOHVTXBIPYES-UHFFFAOYSA-N chembl3277223 Chemical compound C1=CC=C2C(C=3C=NN4C(O)=CC(=NC4=3)O)=CC=CC2=C1 ROYOHVTXBIPYES-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- SYFFHRPDTQNMQB-UHFFFAOYSA-N ethyl 3-oxopropanoate Chemical compound CCOC(=O)CC=O SYFFHRPDTQNMQB-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical class N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17219571A | 1971-08-16 | 1971-08-16 | |
| US261103A US3920652A (en) | 1971-08-16 | 1972-06-08 | Aromatic substituted pyrazola {8 1,5a{9 {0 pyrimidine compounds useful as xanthine oxidase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU522800A3 true SU522800A3 (ru) | 1976-07-25 |
Family
ID=26867834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1821375A SU522800A3 (ru) | 1971-08-16 | 1972-08-15 | Способ получени производных пиразоло (1,5-а) пиримидина |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3920652A (show.php) |
| JP (1) | JPS4834899A (show.php) |
| AR (1) | AR193536A1 (show.php) |
| AT (1) | AT330780B (show.php) |
| BE (1) | BE786611A (show.php) |
| BG (1) | BG19806A3 (show.php) |
| DD (1) | DD99581A5 (show.php) |
| DE (1) | DE2236987A1 (show.php) |
| ES (1) | ES405663A1 (show.php) |
| FR (1) | FR2150771B1 (show.php) |
| GB (1) | GB1359563A (show.php) |
| HU (1) | HU167466B (show.php) |
| IE (1) | IE36629B1 (show.php) |
| IL (1) | IL39988A0 (show.php) |
| LU (1) | LU65892A1 (show.php) |
| MC (1) | MC937A1 (show.php) |
| NL (1) | NL7211011A (show.php) |
| RO (1) | RO63871A (show.php) |
| SU (1) | SU522800A3 (show.php) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4093617A (en) * | 1974-11-12 | 1978-06-06 | Icn Pharmaceuticals, Inc. | 3,5,7-Trisubstituted pyrazolo[1,5-a]pyrimidines |
| US4048184A (en) * | 1976-11-15 | 1977-09-13 | E. R. Squibb & Sons, Inc. | 6-Phenyl-2H-pyrazolo[3,4-b]pyridines |
| US4281000A (en) * | 1979-07-09 | 1981-07-28 | American Cyanamid Company | Substituted pyrazolo (1,5-a)pyrimidines and their use as anxiolytic agents |
| AU557300B2 (en) * | 1982-03-16 | 1986-12-18 | Farmitalia Carlo Erba S.P.A. | Substituted 1h-pyrazolo(1,5-alpha)pyrimidines and processes for their preparation |
| ZA831407B (en) * | 1982-03-25 | 1983-11-30 | Erba Farmitalia | Substituted ethenyl derivatives of 1h-pyrazolo(1,5-a)pyrimidine and process for their preparation |
| WO1992006096A1 (fr) * | 1990-10-09 | 1992-04-16 | Otsuka Pharmaceutical Co., Ltd. | Derive de pyrimidine, production de ce derive et inhibiteur d'androgenes |
| AU667575B2 (en) * | 1992-10-20 | 1996-03-28 | Otsuka Pharmaceutical Co., Ltd. | Condensed pyrazole derivatives, method of manufacturing the same, and androgen inhibitor |
| KR100260292B1 (ko) * | 1995-09-28 | 2000-07-01 | 오쓰카 요시미쓰 | 진통제 |
| US6664261B2 (en) | 1996-02-07 | 2003-12-16 | Neurocrine Biosciences, Inc. | Pyrazolopyrimidines as CRF receptor antagonists |
| US6060478A (en) * | 1996-07-24 | 2000-05-09 | Dupont Pharmaceuticals | Azolo triazines and pyrimidines |
| US6191131B1 (en) | 1997-07-23 | 2001-02-20 | Dupont Pharmaceuticals Company | Azolo triazines and pyrimidines |
| US6313124B1 (en) | 1997-07-23 | 2001-11-06 | Dupont Pharmaceuticals Company | Tetrazine bicyclic compounds |
| US7094782B1 (en) | 1996-07-24 | 2006-08-22 | Bristol-Myers Squibb Company | Azolo triazines and pyrimidines |
| ES2294800T3 (es) * | 1996-07-24 | 2008-04-01 | Bristol-Myers Squibb Pharma Company | Azolo triazinas y pirimidinas. |
| US6124289A (en) * | 1996-07-24 | 2000-09-26 | Dupont Pharmaceuticals Co. | Azolo triazines and pyrimidines |
| US6235741B1 (en) * | 1997-05-30 | 2001-05-22 | Merck & Co., Inc. | Angiogenesis inhibitors |
| WO1999024038A1 (en) * | 1997-11-07 | 1999-05-20 | Johns Hopkins University | Methods for treatment of disorders of cardiac contractility |
| US6380203B1 (en) * | 1998-01-14 | 2002-04-30 | Merck & Co., Inc. | Angiogenesis inhibitors |
| AU4331500A (en) | 1999-04-06 | 2000-10-23 | Du Pont Pharmaceuticals Company | Pyrazolotriazines as crf antagonists |
| WO2000059908A2 (en) | 1999-04-06 | 2000-10-12 | Du Pont Pharmaceuticals Company | Pyrazolopyrimidines as crf antagonists |
| US6630476B2 (en) | 2000-07-07 | 2003-10-07 | Bristol-Myers Squibb Pharma Company | Pyrrolo [3,4-d] pyrimidines as corticotropin releasing factor (CRF) antagonists |
| WO2015186117A1 (en) | 2014-06-06 | 2015-12-10 | Siemens Medical Solutions Usa, Inc. | Gamma camera dead time determination in real time using long lived radioisotopes |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3048587A (en) * | 1960-10-17 | 1962-08-07 | Ortho Pharma Corp | 2-alkylamino-4-aminopyrimidine |
| US3296268A (en) * | 1965-10-19 | 1967-01-03 | Searle & Co | 3-cyanoethyl-2-oxo-5-phenyl [1, 5-a] pyrimidines |
-
0
- BE BE786611D patent/BE786611A/xx unknown
-
1972
- 1972-06-08 US US261103A patent/US3920652A/en not_active Expired - Lifetime
- 1972-07-25 IL IL39988A patent/IL39988A0/xx unknown
- 1972-07-27 DE DE2236987A patent/DE2236987A1/de active Pending
- 1972-08-02 MC MC1005A patent/MC937A1/fr unknown
- 1972-08-04 AT AT677372A patent/AT330780B/de not_active IP Right Cessation
- 1972-08-07 GB GB3680472A patent/GB1359563A/en not_active Expired
- 1972-08-08 ES ES405663A patent/ES405663A1/es not_active Expired
- 1972-08-08 AR AR243489A patent/AR193536A1/es active
- 1972-08-08 IE IE1107/72A patent/IE36629B1/xx unknown
- 1972-08-11 FR FR7229107A patent/FR2150771B1/fr not_active Expired
- 1972-08-11 NL NL7211011A patent/NL7211011A/xx unknown
- 1972-08-11 LU LU65892A patent/LU65892A1/xx unknown
- 1972-08-14 BG BG021195A patent/BG19806A3/xx unknown
- 1972-08-14 DD DD165054A patent/DD99581A5/xx unknown
- 1972-08-15 HU HUIE526A patent/HU167466B/hu unknown
- 1972-08-15 SU SU1821375A patent/SU522800A3/ru active
- 1972-08-16 RO RO7200071971A patent/RO63871A/ro unknown
- 1972-08-16 JP JP47082059A patent/JPS4834899A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US3920652A (en) | 1975-11-18 |
| RO63871A (fr) | 1979-01-15 |
| BE786611A (fr) | 1973-01-22 |
| IL39988A0 (en) | 1972-09-28 |
| GB1359563A (en) | 1974-07-10 |
| ATA677372A (de) | 1975-10-15 |
| IE36629L (en) | 1973-02-16 |
| NL7211011A (show.php) | 1973-02-20 |
| FR2150771A1 (show.php) | 1973-04-13 |
| BG19806A3 (bg) | 1975-10-10 |
| AR193536A1 (es) | 1973-04-30 |
| IE36629B1 (en) | 1977-01-19 |
| AT330780B (de) | 1976-07-26 |
| MC937A1 (fr) | 1973-08-10 |
| DE2236987A1 (de) | 1973-03-01 |
| DD99581A5 (show.php) | 1973-08-12 |
| HU167466B (show.php) | 1975-10-28 |
| ES405663A1 (es) | 1976-01-16 |
| FR2150771B1 (show.php) | 1976-05-21 |
| LU65892A1 (show.php) | 1973-01-15 |
| JPS4834899A (show.php) | 1973-05-22 |
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