CS199690B2 - Způsob výroby spiro-hydantoinových derivátů - Google Patents
Způsob výroby spiro-hydantoinových derivátů Download PDFInfo
- Publication number
- CS199690B2 CS199690B2 CS776770A CS677077A CS199690B2 CS 199690 B2 CS199690 B2 CS 199690B2 CS 776770 A CS776770 A CS 776770A CS 677077 A CS677077 A CS 677077A CS 199690 B2 CS199690 B2 CS 199690B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- spiro
- dione
- imidazolidine
- fluoro
- alkali metal
- Prior art date
Links
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 30
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- 239000007884 disintegrant Substances 0.000 description 1
- MQRJBSHKWOFOGF-UHFFFAOYSA-L disodium;carbonate;hydrate Chemical compound O.[Na+].[Na+].[O-]C([O-])=O MQRJBSHKWOFOGF-UHFFFAOYSA-L 0.000 description 1
- FMWAXKQEIXRUTI-UHFFFAOYSA-N dodecyl hydrogen sulfate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(O)(=O)=O FMWAXKQEIXRUTI-UHFFFAOYSA-N 0.000 description 1
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- BCZQNQXJPMUTQA-UHFFFAOYSA-N ethyl 3-(4-fluorophenyl)-1,2,4-oxadiazole-5-carboxylate Chemical compound O1C(C(=O)OCC)=NC(C=2C=CC(F)=CC=2)=N1 BCZQNQXJPMUTQA-UHFFFAOYSA-N 0.000 description 1
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- QSCPWUQGLBXOJB-UHFFFAOYSA-N methyl 2-amino-5-(3-fluorophenyl)-1,3-thiazole-4-carboxylate Chemical compound N1=C(N)SC(C=2C=C(F)C=CC=2)=C1C(=O)OC QSCPWUQGLBXOJB-UHFFFAOYSA-N 0.000 description 1
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- 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 1
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- 235000011803 sesame oil Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229940076133 sodium carbonate monohydrate Drugs 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- VRWLKAXHAFPEHR-UHFFFAOYSA-N spiro[5,6-dihydrocyclopenta[f][1,3]benzodioxole-7,5'-imidazolidine]-2',4'-dione Chemical compound N1C(=O)NC(=O)C11C2=CC(OCO3)=C3C=C2CC1 VRWLKAXHAFPEHR-UHFFFAOYSA-N 0.000 description 1
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- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- 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
- C07D487/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73306276A | 1976-10-18 | 1976-10-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS199690B2 true CS199690B2 (cs) | 1980-07-31 |
Family
ID=24946075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS776770A CS199690B2 (cs) | 1976-10-18 | 1977-10-18 | Způsob výroby spiro-hydantoinových derivátů |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4117230A (pl) |
| BE (1) | BE859824A (pl) |
| CS (1) | CS199690B2 (pl) |
| HU (1) | HU177716B (pl) |
| IN (1) | IN147056B (pl) |
| PL (1) | PL108339B1 (pl) |
| SU (1) | SU741795A3 (pl) |
| ZA (1) | ZA775907B (pl) |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4147797A (en) * | 1978-08-11 | 1979-04-03 | Pfizer Inc. | Spiro-furanohydantoin derivatives |
| US4181728A (en) * | 1978-11-16 | 1980-01-01 | Pfizer Inc. | Spiro-polycyclicimidazolidinedione derivatives |
| US4176185A (en) * | 1979-01-22 | 1979-11-27 | Pfizer Inc. | Spiro-quinolylhydantoins |
| US4181729A (en) * | 1979-03-21 | 1980-01-01 | Pfizer Inc. | Phenyl or phenoxy substituted spiro-imidazolidinedione derivatives |
| US4193996A (en) * | 1979-04-04 | 1980-03-18 | Pfizer Inc. | Spiro-quinolone hydantoins |
| US4210667A (en) * | 1979-04-19 | 1980-07-01 | Pfizer Inc. | Pharmaceutical preparations containing coumarin carboxylic acid derivatives |
| US4490381A (en) * | 1979-11-13 | 1984-12-25 | Imperial Chemical Industries Plc | 1'-Substituted spiro[imidazolidine-4,3'-indoline]2,2',5-triones |
| US4248882A (en) * | 1980-02-12 | 1981-02-03 | Pfizer Inc. | Treating diabetes-associated complications with hydantoin amines |
| US4348526A (en) * | 1980-03-28 | 1982-09-07 | Pfizer Inc. | Intermediates in the preparation of chiral hydantoins |
| US4286098A (en) * | 1980-03-28 | 1981-08-25 | Pfizer Inc. | Process for the preparation of chiral hydantoins |
| JPS5745185A (en) * | 1980-07-21 | 1982-03-13 | Eisai Co Ltd | Hydantoin derivative and its preparation |
| IE53102B1 (en) * | 1981-05-12 | 1988-06-22 | Ici Plc | Pharmaceutical spiro-succinimide derivatives |
| DE3261684D1 (en) * | 1981-05-12 | 1985-02-07 | Ici Plc | Pyrrole derivatives |
| IE52879B1 (en) * | 1981-05-12 | 1988-03-30 | Ici Plc | Pharmaceutical spiro-hydantoin derivatives |
| ATE11781T1 (de) * | 1981-05-13 | 1985-02-15 | Imperial Chemical Industries Plc | Pharmazeutische zubereitungen, die spirosuccinimidderivate enthalten. |
| US4419521A (en) * | 1981-11-12 | 1983-12-06 | Pfizer Inc. | 6-Halo-4-chromanamines useful as intermediates to make chiral hydantoins |
| US4464385A (en) * | 1982-04-15 | 1984-08-07 | Alcon Laboratories, Inc. | Treatment of diabetic complications with hydantoins |
| US4540700A (en) * | 1982-04-15 | 1985-09-10 | Alcon Laboratories, Inc. | Treatment of diabetic complications with certain spiro-imidazolidine-diones |
| US4436745A (en) | 1982-04-15 | 1984-03-13 | Alcon Laboratories, Inc. | Method of inhibiting aldose reductase activity |
| US4438272A (en) | 1982-04-15 | 1984-03-20 | Alcon Laboratories, Inc. | Spiro-(fluoren-9,4'-imidazolidine)-2',5'-diones |
| IL68314A0 (en) * | 1982-04-15 | 1983-07-31 | Alcon Lab Inc | Method and composition for inhibiting aldose reductase activity and process for preparing spirofluorofluoren and spiro-difluorofluoren compounds |
| US4435578A (en) | 1982-11-10 | 1984-03-06 | Pfizer Inc. | Sorbinil by optical resolution of precursor 6-fluoro-4-ureidochroman-4-carboxylic acid |
| US4528387A (en) * | 1982-11-10 | 1985-07-09 | Pfizer Inc. | Sorbinil by optical resolution of precursor 6-fluoro-4-ureidochroman-4-carboxylic acid |
| US4556670A (en) * | 1982-12-06 | 1985-12-03 | Pfizer Inc. | Spiro-3-hetero-azolones for treatment of diabetic complications |
| US4474967A (en) * | 1983-04-27 | 1984-10-02 | Pfizer Inc. | 8-Deutero and 8-tritio-substituted derivatives of D-4S-6-fluoro-spiro-[chroman-4,4'-imidazolidine]-2',5'-dione |
| US5153211A (en) * | 1983-09-14 | 1992-10-06 | Alcon Laboratories, Inc. | Spiro-tricyclicaromatic succinimide derivatives as inhibitors of aldose reductase |
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| DE3561198D1 (en) * | 1984-03-23 | 1988-01-28 | Pfizer | Spiro-indenes and spiro-1,2-dihydro-naphthalenes for treatment of diabetic complications |
| US4600717A (en) * | 1984-04-11 | 1986-07-15 | Alcon Laboratories, Inc. | Aldose reductase inhibitors useful in ophthalmic wound healing |
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| US5066659A (en) * | 1984-10-30 | 1991-11-19 | Pfizer Inc. | Spiro-heteroazalones for treatment of diabetic complications |
| US4575507A (en) | 1985-05-29 | 1986-03-11 | Pfizer Inc. | Spiro-imidazolidines as aldose reductase inhibitors and their pharmaceutical use |
| US4762839A (en) * | 1985-06-06 | 1988-08-09 | Tanabe Seiyaku Co., Ltd. | Quinazolinone copmpounds useful for the prophyloxis and treatment of diabetic complications |
| WO1986007353A1 (en) | 1985-06-14 | 1986-12-18 | Pfizer Inc. | Intermediate in the production of an asymmetric hydantoin |
| US4853410A (en) * | 1986-01-17 | 1989-08-01 | Pfizer Inc. | Hydroxyacetic acid derivatives for the treatment of diabetic complications |
| US4853401A (en) * | 1987-04-01 | 1989-08-01 | G. D. Searle & Co. | Spiro-hydantoins as aldose reductase inhibitors |
| US4841079A (en) * | 1987-08-07 | 1989-06-20 | Pfizer, Inc. | Process for the production of asymmetric hydantoins |
| US5006657A (en) * | 1988-07-27 | 1991-04-09 | Pfizer Inc. | Intermediates in a resolution process for racemic spiro hydantoins |
| US4952694A (en) * | 1988-07-27 | 1990-08-28 | Pfizer Inc. | Novel resolution process for racemic spiro-hydantoins |
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| US5151544A (en) * | 1990-05-25 | 1992-09-29 | Alcon Laboratories, Inc. | Intermediates in the preparation of chiral spirofluorenehydantoins |
| GB2355264A (en) | 1999-09-30 | 2001-04-18 | Merck & Co Inc | Spirohydantoin derivatives useful as alpha 1a adrenoceptor antagonists |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2716648A (en) * | 1955-08-30 | Hydantoin derivatives | ||
| US2683718A (en) * | 1952-01-11 | 1954-07-13 | Searle & Co | Spiro-[xanthene-9, 4'-imidazolidine]-2, 5-dione |
| DE1135915B (de) * | 1961-06-29 | 1962-09-06 | Asta Werke Ag Chem Fab | Verfahren zur Herstellung neuer, antikonvulsiv wirksamer Spirohydantoine |
| US3532744A (en) * | 1967-07-28 | 1970-10-06 | American Home Prod | 1- and 2-amino substituted indane and tetralene carboxylic acids |
-
1977
- 1977-02-11 US US05/767,803 patent/US4117230A/en not_active Expired - Lifetime
- 1977-10-04 ZA ZA00775907A patent/ZA775907B/xx unknown
- 1977-10-05 IN IN294/DEL/77A patent/IN147056B/en unknown
- 1977-10-17 SU SU772535554A patent/SU741795A3/ru active
- 1977-10-17 BE BE181825A patent/BE859824A/xx not_active IP Right Cessation
- 1977-10-17 HU HU77PI594A patent/HU177716B/hu not_active IP Right Cessation
- 1977-10-18 PL PL1977201586A patent/PL108339B1/pl unknown
- 1977-10-18 CS CS776770A patent/CS199690B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US4117230A (en) | 1978-09-26 |
| HU177716B (en) | 1981-12-28 |
| IN147056B (pl) | 1979-10-27 |
| ZA775907B (en) | 1978-05-30 |
| PL201586A1 (pl) | 1978-09-25 |
| BE859824A (fr) | 1978-04-17 |
| PL108339B1 (en) | 1980-04-30 |
| SU741795A3 (ru) | 1980-06-15 |
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