SU897110A3 - Способ получени рацемического моногидрата дигидрохлорида 3-/2-(3-трет.бутиламино-2-оксипропокси)фенил/-6-гидразинпиридазина - Google Patents
Способ получени рацемического моногидрата дигидрохлорида 3-/2-(3-трет.бутиламино-2-оксипропокси)фенил/-6-гидразинпиридазина Download PDFInfo
- Publication number
- SU897110A3 SU897110A3 SU782660649A SU2660649A SU897110A3 SU 897110 A3 SU897110 A3 SU 897110A3 SU 782660649 A SU782660649 A SU 782660649A SU 2660649 A SU2660649 A SU 2660649A SU 897110 A3 SU897110 A3 SU 897110A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- water
- monohydrate
- phenyl
- tert
- racemic
- Prior art date
Links
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 title description 19
- 238000000034 method Methods 0.000 title description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 28
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- BAFOEQOGYLVKNR-UHFFFAOYSA-N 1-(tert-butylamino)-3-[2-(6-hydrazinylpyridazin-3-yl)phenoxy]propan-2-ol;hydrate;dihydrochloride Chemical compound O.Cl.Cl.CC(C)(C)NCC(O)COC1=CC=CC=C1C1=CC=C(NN)N=N1 BAFOEQOGYLVKNR-UHFFFAOYSA-N 0.000 abstract 1
- 230000003276 anti-hypertensive effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 12
- -1 (3-tert-butylamino-2-hydroxypropoxy) phenyl Chemical group 0.000 description 10
- 150000004682 monohydrates Chemical class 0.000 description 9
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000002585 base Substances 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 239000003921 oil Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000012458 free base Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- WFNVFNILGYZHHK-UHFFFAOYSA-N hydrazine;pyridazine Chemical compound NN.C1=CC=NN=C1 WFNVFNILGYZHHK-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- BUBRFWDEAVIFMV-UHFFFAOYSA-N 3-chloro-6-phenylpyridazine Chemical compound N1=NC(Cl)=CC=C1C1=CC=CC=C1 BUBRFWDEAVIFMV-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- RDCGVLDOUGPLLK-UHFFFAOYSA-N C(C)(C)(C)NCC(COC=1C(N(N=CC1)C1=CC=CC=C1)=S)O Chemical compound C(C)(C)(C)NCC(COC=1C(N(N=CC1)C1=CC=CC=C1)=S)O RDCGVLDOUGPLLK-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- QHFQAJHNDKBRBO-UHFFFAOYSA-L calcium chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Ca+2] QHFQAJHNDKBRBO-UHFFFAOYSA-L 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229920001577 copolymer Chemical group 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- JKXCZYCVHPKTPK-UHFFFAOYSA-N hydrate;trihydrochloride Chemical compound O.Cl.Cl.Cl JKXCZYCVHPKTPK-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having 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
- C07D237/20—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7832312 | 1978-08-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU897110A3 true SU897110A3 (ru) | 1982-01-07 |
Family
ID=10498866
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782660649A SU897110A3 (ru) | 1978-08-04 | 1978-09-04 | Способ получени рацемического моногидрата дигидрохлорида 3-/2-(3-трет.бутиламино-2-оксипропокси)фенил/-6-гидразинпиридазина |
Country Status (29)
| Country | Link |
|---|---|
| EP (1) | EP0007930B1 (enExample) |
| JP (1) | JPS6040424B2 (enExample) |
| AR (1) | AR223327A1 (enExample) |
| AT (1) | AT361001B (enExample) |
| BG (1) | BG34335A3 (enExample) |
| CA (1) | CA1098522A (enExample) |
| CS (1) | CS204035B2 (enExample) |
| DD (1) | DD138656A5 (enExample) |
| DE (1) | DE2862214D1 (enExample) |
| DK (1) | DK147761C (enExample) |
| EG (1) | EG13469A (enExample) |
| ES (1) | ES473056A1 (enExample) |
| FI (1) | FI64585C (enExample) |
| GR (1) | GR64897B (enExample) |
| HU (1) | HU181959B (enExample) |
| IE (1) | IE47555B1 (enExample) |
| IL (1) | IL55455A (enExample) |
| IN (1) | IN148775B (enExample) |
| IT (1) | IT1110169B (enExample) |
| MT (1) | MTP851B (enExample) |
| MX (1) | MX5425E (enExample) |
| NO (1) | NO783005L (enExample) |
| NZ (1) | NZ188281A (enExample) |
| OA (1) | OA06046A (enExample) |
| PL (1) | PL119444B1 (enExample) |
| SU (1) | SU897110A3 (enExample) |
| YU (1) | YU209078A (enExample) |
| ZA (1) | ZA785008B (enExample) |
| ZM (1) | ZM8078A1 (enExample) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE42214B1 (en) * | 1974-06-18 | 1980-07-02 | Smith Kline French Lab | Hydrazinopyredazines |
-
1978
- 1978-08-21 IN IN619/DEL/78A patent/IN148775B/en unknown
- 1978-08-22 IE IE1702/78A patent/IE47555B1/en unknown
- 1978-08-28 NZ NZ188281A patent/NZ188281A/xx unknown
- 1978-08-28 GR GR57100A patent/GR64897B/el unknown
- 1978-08-29 IL IL55455A patent/IL55455A/xx unknown
- 1978-08-29 JP JP53106180A patent/JPS6040424B2/ja not_active Expired
- 1978-08-30 EG EG541/78A patent/EG13469A/xx active
- 1978-08-31 IT IT27234/78A patent/IT1110169B/it active
- 1978-09-01 HU HU78SI1646A patent/HU181959B/hu unknown
- 1978-09-01 ZA ZA00785008A patent/ZA785008B/xx unknown
- 1978-09-01 CA CA310,530A patent/CA1098522A/en not_active Expired
- 1978-09-04 EP EP78300341A patent/EP0007930B1/en not_active Expired
- 1978-09-04 YU YU02090/78A patent/YU209078A/xx unknown
- 1978-09-04 PL PL1978209407A patent/PL119444B1/pl unknown
- 1978-09-04 OA OA56598A patent/OA06046A/xx unknown
- 1978-09-04 ES ES473056A patent/ES473056A1/es not_active Expired
- 1978-09-04 BG BG040811A patent/BG34335A3/xx unknown
- 1978-09-04 DD DD78207634A patent/DD138656A5/xx unknown
- 1978-09-04 DE DE7878300341T patent/DE2862214D1/de not_active Expired
- 1978-09-04 CS CS785723A patent/CS204035B2/cs unknown
- 1978-09-04 AT AT638378A patent/AT361001B/de not_active IP Right Cessation
- 1978-09-04 NO NO783005A patent/NO783005L/no unknown
- 1978-09-04 DK DK389378A patent/DK147761C/da not_active IP Right Cessation
- 1978-09-04 MX MX787372U patent/MX5425E/es unknown
- 1978-09-04 FI FI782705A patent/FI64585C/fi not_active IP Right Cessation
- 1978-09-04 SU SU782660649A patent/SU897110A3/ru active
- 1978-09-05 AR AR273573A patent/AR223327A1/es active
- 1978-09-15 ZM ZM80/78A patent/ZM8078A1/xx unknown
-
1979
- 1979-07-23 MT MT851A patent/MTP851B/xx unknown
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