SU1380610A3 - Способ получени спирогетероазолидиндионов или их фармацевтически приемлемых солей - Google Patents
Способ получени спирогетероазолидиндионов или их фармацевтически приемлемых солей Download PDFInfo
- Publication number
- SU1380610A3 SU1380610A3 SU833674609A SU3674609A SU1380610A3 SU 1380610 A3 SU1380610 A3 SU 1380610A3 SU 833674609 A SU833674609 A SU 833674609A SU 3674609 A SU3674609 A SU 3674609A SU 1380610 A3 SU1380610 A3 SU 1380610A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- alkyl
- continuation
- hydrogen
- dione
- compounds
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 150000003839 salts Chemical class 0.000 title abstract description 8
- 102000016912 Aldehyde Reductase Human genes 0.000 claims abstract description 7
- 108010053754 Aldehyde reductase Proteins 0.000 claims abstract description 7
- 230000005764 inhibitory process Effects 0.000 claims abstract description 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract 4
- 125000005843 halogen group Chemical group 0.000 claims abstract 3
- 150000002367 halogens Chemical class 0.000 claims abstract 3
- 102000004190 Enzymes Human genes 0.000 claims abstract 2
- 108090000790 Enzymes Proteins 0.000 claims abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 2
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 239000001301 oxygen Substances 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 34
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 5
- 239000000600 sorbitol Substances 0.000 claims description 5
- 210000002826 placenta Anatomy 0.000 claims description 4
- 210000003497 sciatic nerve Anatomy 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims 5
- ZSJLQEPLLKMAKR-UHFFFAOYSA-N Streptozotocin Natural products O=NN(C)C(=O)NC1C(O)OC(CO)C(O)C1O ZSJLQEPLLKMAKR-UHFFFAOYSA-N 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 claims 4
- 229960001052 streptozocin Drugs 0.000 claims 4
- 241000700159 Rattus Species 0.000 claims 3
- 241001465754 Metazoa Species 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 244000309466 calf Species 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 11
- 229920000137 polyphosphoric acid Polymers 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 3
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
- 210000000056 organ Anatomy 0.000 abstract description 2
- 231100000161 signs of toxicity Toxicity 0.000 abstract description 2
- 230000000007 visual effect Effects 0.000 abstract description 2
- NZNUMNLHZBSSJW-UHFFFAOYSA-N 2-(2,5-dioxo-4-phenylimidazolidin-4-yl)acetic acid Chemical compound C=1C=CC=CC=1C1(CC(=O)O)NC(=O)NC1=O NZNUMNLHZBSSJW-UHFFFAOYSA-N 0.000 abstract 1
- 239000013543 active substance Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 239000007787 solid Substances 0.000 description 29
- AZRRZGIBBLWSSQ-UHFFFAOYSA-N 4-ethyl-7-phenyl-3,5-diazabicyclo[2.2.2]octane-2,6-dione Chemical compound N1C(=O)C2C(=O)NC1(CC)CC2C1=CC=CC=C1 AZRRZGIBBLWSSQ-UHFFFAOYSA-N 0.000 description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 22
- 238000001914 filtration Methods 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- ZYKVRFMMRAPHAZ-UHFFFAOYSA-N 7-fluoro-3 Chemical compound C1S(=O)(=O)CC(C=2)=CC(F)=CC=2CS(=O)(=O)CC2=CC=C1C=C2 ZYKVRFMMRAPHAZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000005909 Kieselgur Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 125000003003 spiro group Chemical group 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- RRKTZKIUPZVBMF-IBTVXLQLSA-O (4ar,5as,8as,13as,15as,15br)-10,11-dimethoxy-2,4a,5,5a,6,7,8,13a,15,15a,15b,16-dodecahydro4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinoline-6-ium-14-one Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2C[NH+]2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-O 0.000 description 1
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 description 1
- RUWPCCQWDIAGAJ-UHFFFAOYSA-N 3-(2,5-dioxo-4-phenylimidazolidin-4-yl)propanoic acid Chemical compound C=1C=CC=CC=1C1(CCC(=O)O)NC(=O)NC1=O RUWPCCQWDIAGAJ-UHFFFAOYSA-N 0.000 description 1
- COJDKHNHTGNTTO-UHFFFAOYSA-N 3-[4-(3-chloro-4-methylphenyl)-2,5-dioxoimidazolidin-4-yl]propanoic acid Chemical compound C1=C(Cl)C(C)=CC=C1C1(CCC(O)=O)C(=O)NC(=O)N1 COJDKHNHTGNTTO-UHFFFAOYSA-N 0.000 description 1
- PCBVBKXPFTVQJH-UHFFFAOYSA-N 3-[4-(3-chlorophenyl)-2,5-dioxoimidazolidin-4-yl]propanoic acid Chemical compound C=1C=CC(Cl)=CC=1C1(CCC(=O)O)NC(=O)NC1=O PCBVBKXPFTVQJH-UHFFFAOYSA-N 0.000 description 1
- KXXLCMPSLFIEEH-UHFFFAOYSA-N 4h-naphthalene-1,3-dione Chemical compound C1=CC=C2CC(=O)CC(=O)C2=C1 KXXLCMPSLFIEEH-UHFFFAOYSA-N 0.000 description 1
- 208000002249 Diabetes Complications Diseases 0.000 description 1
- 206010012655 Diabetic complications Diseases 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 239000003738 black carbon Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- -1 m-fluorophenyl compound Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44733782A | 1982-12-06 | 1982-12-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1380610A3 true SU1380610A3 (ru) | 1988-03-07 |
Family
ID=23775964
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU833674609A SU1380610A3 (ru) | 1982-12-06 | 1983-12-05 | Способ получени спирогетероазолидиндионов или их фармацевтически приемлемых солей |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS59116274A (enrdf_load_stackoverflow) |
| CS (1) | CS244683B2 (enrdf_load_stackoverflow) |
| DD (1) | DD234265A5 (enrdf_load_stackoverflow) |
| HU (1) | HU193191B (enrdf_load_stackoverflow) |
| IN (1) | IN160449B (enrdf_load_stackoverflow) |
| SU (1) | SU1380610A3 (enrdf_load_stackoverflow) |
| ZA (1) | ZA839023B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2448096C2 (ru) * | 2005-05-13 | 2012-04-20 | Те Риджентс Оф Те Юниверсити Оф Калифорния | Диарилгидантоины |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4575507A (en) * | 1985-05-29 | 1986-03-11 | Pfizer Inc. | Spiro-imidazolidines as aldose reductase inhibitors and their pharmaceutical use |
| GB2355264A (en) | 1999-09-30 | 2001-04-18 | Merck & Co Inc | Spirohydantoin derivatives useful as alpha 1a adrenoceptor antagonists |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1088945A (en) * | 1976-10-18 | 1980-11-04 | Pfizer Limited | Hydantoin derivatives as therapeutic agents |
| US4181729A (en) * | 1979-03-21 | 1980-01-01 | Pfizer Inc. | Phenyl or phenoxy substituted spiro-imidazolidinedione derivatives |
-
1983
- 1983-12-05 SU SU833674609A patent/SU1380610A3/ru active
- 1983-12-05 ZA ZA839023A patent/ZA839023B/xx unknown
- 1983-12-05 HU HU416183A patent/HU193191B/hu not_active IP Right Cessation
- 1983-12-06 DD DD27521983A patent/DD234265A5/de not_active IP Right Cessation
- 1983-12-06 JP JP23048683A patent/JPS59116274A/ja active Granted
- 1983-12-06 CS CS839130A patent/CS244683B2/cs unknown
- 1983-12-14 IN IN838/DEL/83A patent/IN160449B/en unknown
Non-Patent Citations (1)
| Title |
|---|
| Патент US № 4226875, кл. 424-272, опублик. 1981. , К.Бюлер, Д.Пирсон, Органические синтезы. М.: Мир, 1972, ч. 2. с. 123-125. * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2448096C2 (ru) * | 2005-05-13 | 2012-04-20 | Те Риджентс Оф Те Юниверсити Оф Калифорния | Диарилгидантоины |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59116274A (ja) | 1984-07-05 |
| ZA839023B (en) | 1985-07-31 |
| CS244683B2 (en) | 1986-08-14 |
| HU193191B (en) | 1987-08-28 |
| DD234265A5 (de) | 1986-03-26 |
| CS913083A2 (en) | 1985-09-17 |
| JPH0251548B2 (enrdf_load_stackoverflow) | 1990-11-07 |
| IN160449B (enrdf_load_stackoverflow) | 1987-07-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2914494C2 (enrdf_load_stackoverflow) | ||
| DE69723846T2 (de) | Verfahren zur Herstellung von Sildenafil | |
| JPH0737460B2 (ja) | ピラノインドリジン誘導体及びその製造法 | |
| DE3010195C2 (enrdf_load_stackoverflow) | ||
| US4007169A (en) | Method of preparing derivatives of rifamycin S | |
| SU1138029A3 (ru) | Способ получени 5-замещенных 1,2-дигидро-3 @ -пирроло- @ 1,2 @ -пиррол-1-карбоновых кислот | |
| SU1380610A3 (ru) | Способ получени спирогетероазолидиндионов или их фармацевтически приемлемых солей | |
| McEwen et al. | 1, 3-Dipolar addition reactions of Reissert compounds | |
| CH520680A (de) | Verfahren zur Herstellung neuer Mutterkornpeptidalkaloide | |
| US4284797A (en) | Process for separating mixtures of 3- and 4-nitrophthalic acid | |
| US4125558A (en) | Method for the manufacture of the cis-2-hydroxy-2-phenyl-r-1-cyclohexanecarboxylic acid | |
| DE3028369A1 (de) | Verfahren zur herstellung von 7-alkoxycarbonyl-6,8-dimethyl-4-hydroxymethyl-1-phthalazon und die dabei auftretenden zwischenprodukte | |
| KR100704641B1 (ko) | 고순도의 레보플록사신 제조방법 | |
| KR100827898B1 (ko) | 클라불란산의 염의 정제 방법 | |
| EP0025941B1 (de) | Pyridazopyridazinderivate, Verfahren zu deren Herstellung und Arzneimittel enthaltend solche Pyridazopyridazinderivate | |
| KR102836734B1 (ko) | 소디움 타우로디옥시콜레이트의 대량 생산 방법 | |
| SU554816A3 (ru) | Способ получени азотсодержащих полициклических соединений или их солей, или рацематов, или оптических антиподов | |
| SU645584A3 (ru) | Способ получени рифамициновых соединений их 16,17,18,19-тетрагидроили 16,17,18,19,28,29-гексагидропроизводных | |
| DE1670248B2 (de) | Verfahren zur Herstellung von 4-Isothiazolcarbonsäuren | |
| SU831078A3 (ru) | Способ получени цис-изомера ,-ди-МЕТил-9- 3-(4-МЕТил-1-пипЕРАзиНил)пРОпилидЕН -ТиОКСАНТЕН -2-СульфАМидА | |
| KR920010638B1 (ko) | 1,1-비스(4-클로로페닐)-2,2,2-트리클로로에탄올의 제조방법. | |
| DE2906253A1 (de) | Furonaphthyridinverbindungen und arzneimittel | |
| SU645565A3 (ru) | Способ получени производных пиридина | |
| SU1587053A1 (ru) | Способ получени 2,3-дигидро-1Н-пирроло-(1,2- @ )бензимидазол-6-сульфокислоты | |
| LU86853A1 (de) | Neue 8-beziehungsweise 1,8-substituierte ergolenderivate und verfahren zu ihrer herstellung |