SU852171A3 - Способ получени производных ОКСиТиАзОлидиНТиОКЕТОНА или иХ СОлЕй - Google Patents
Способ получени производных ОКСиТиАзОлидиНТиОКЕТОНА или иХ СОлЕй Download PDFInfo
- Publication number
- SU852171A3 SU852171A3 SU782615706A SU2615706A SU852171A3 SU 852171 A3 SU852171 A3 SU 852171A3 SU 782615706 A SU782615706 A SU 782615706A SU 2615706 A SU2615706 A SU 2615706A SU 852171 A3 SU852171 A3 SU 852171A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- pyridyl
- alkyl
- carbon atoms
- dithiocarbamate
- product
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- 150000003839 salts Chemical class 0.000 title claims description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 30
- 239000000047 product Substances 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 238000002844 melting Methods 0.000 claims description 17
- 230000008018 melting Effects 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 238000001953 recrystallisation Methods 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
- -1 tri-ammonium 2-pyridyldithiocarbamate Chemical compound 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- ZERJVEQLQZTTQS-UHFFFAOYSA-N n,n-diethylethanamine;pyridin-2-ylcarbamodithioic acid Chemical compound CCN(CC)CC.SC(=S)NC1=CC=CC=N1 ZERJVEQLQZTTQS-UHFFFAOYSA-N 0.000 claims description 9
- 239000012153 distilled water Substances 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 239000012990 dithiocarbamate Substances 0.000 claims description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 5
- 239000000377 silicon dioxide Substances 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 229910052736 halogen Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 235000019271 petrolatum Nutrition 0.000 claims description 3
- 229940099259 vaseline Drugs 0.000 claims description 3
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000004423 acyloxy group Chemical group 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 150000002367 halogens Chemical group 0.000 claims 3
- 239000004264 Petrolatum Substances 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 229940066842 petrolatum Drugs 0.000 claims 2
- HAXAPAKUJJUBIR-UHFFFAOYSA-N 1-chlorodecan-2-one Chemical compound CCCCCCCCC(=O)CCl HAXAPAKUJJUBIR-UHFFFAOYSA-N 0.000 claims 1
- KLQMFXYLBYWLCX-UHFFFAOYSA-N 2-chloro-1-cyclobutylethanone Chemical compound ClCC(=O)C1CCC1 KLQMFXYLBYWLCX-UHFFFAOYSA-N 0.000 claims 1
- ZXWAHROJUXWVCU-UHFFFAOYSA-N 2-chloro-1-cyclopropylethanone Chemical compound ClCC(=O)C1CC1 ZXWAHROJUXWVCU-UHFFFAOYSA-N 0.000 claims 1
- 241000282465 Canis Species 0.000 claims 1
- 231100000111 LD50 Toxicity 0.000 claims 1
- 241000244011 Litomosoides Species 0.000 claims 1
- 241000700159 Rattus Species 0.000 claims 1
- 241000571986 Uncinaria Species 0.000 claims 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims 1
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 238000007664 blowing Methods 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 1
- 150000004659 dithiocarbamates Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000012264 purified product Substances 0.000 claims 1
- 231100000241 scar Toxicity 0.000 claims 1
- 231100000419 toxicity Toxicity 0.000 claims 1
- 230000001988 toxicity Effects 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000009835 boiling Methods 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 10
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 7
- WZQDRRLBAPWQMS-UHFFFAOYSA-N pyridin-2-ylcarbamodithioic acid Chemical compound SC(=S)NC1=CC=CC=N1 WZQDRRLBAPWQMS-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 3
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- LQKQGYIKTRJVJF-UHFFFAOYSA-N (3-chloro-4-oxopentyl) acetate Chemical compound CC(=O)OCCC(Cl)C(C)=O LQKQGYIKTRJVJF-UHFFFAOYSA-N 0.000 description 1
- IEMUUZKOMRJGHD-UHFFFAOYSA-N (5-chloropyridin-2-yl)carbamodithioic acid Chemical compound SC(=S)NC1=CC=C(Cl)C=N1 IEMUUZKOMRJGHD-UHFFFAOYSA-N 0.000 description 1
- CFJJZNJUFTVCLA-UHFFFAOYSA-N (5-chloropyridin-2-yl)carbamodithioic acid;n,n-diethylethanamine Chemical compound CC[NH+](CC)CC.[S-]C(=S)NC1=CC=C(Cl)C=N1 CFJJZNJUFTVCLA-UHFFFAOYSA-N 0.000 description 1
- SAIRZMWXVJEBMO-UHFFFAOYSA-N 1-bromo-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)CBr SAIRZMWXVJEBMO-UHFFFAOYSA-N 0.000 description 1
- AALRHBLMAVGWRR-UHFFFAOYSA-N 1-chlorobutan-2-one Chemical compound CCC(=O)CCl AALRHBLMAVGWRR-UHFFFAOYSA-N 0.000 description 1
- FVXNLWRKEVZHKO-UHFFFAOYSA-N 1-chlorohexan-2-one Chemical compound CCCCC(=O)CCl FVXNLWRKEVZHKO-UHFFFAOYSA-N 0.000 description 1
- ASJANZXGKBBVDY-UHFFFAOYSA-N 1-chlorononan-2-one Chemical compound CCCCCCCC(=O)CCl ASJANZXGKBBVDY-UHFFFAOYSA-N 0.000 description 1
- MGTGUEKJBFTQQW-UHFFFAOYSA-N 1-chloropentan-2-one Chemical compound CCCC(=O)CCl MGTGUEKJBFTQQW-UHFFFAOYSA-N 0.000 description 1
- PUPDAQGFJMQNBK-UHFFFAOYSA-N 2-bromo-2-methylpropan-1-ol Chemical compound CC(C)(Br)CO PUPDAQGFJMQNBK-UHFFFAOYSA-N 0.000 description 1
- DBTWOTKWIVISQR-UHFFFAOYSA-N 2-bromopropan-1-ol Chemical compound CC(Br)CO DBTWOTKWIVISQR-UHFFFAOYSA-N 0.000 description 1
- QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 1
- XHCWDDGZFBAXRT-UHFFFAOYSA-N 3-bromo-3-methylbutan-2-one Chemical compound CC(=O)C(C)(C)Br XHCWDDGZFBAXRT-UHFFFAOYSA-N 0.000 description 1
- GLEVURYDLJLLAP-UHFFFAOYSA-N 4-bromo-5-oxohexanoic acid Chemical compound BrC(CCC(=O)O)C(C)=O GLEVURYDLJLLAP-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- NVVNISHGUAJVFR-UHFFFAOYSA-N C(C(C)C(C(=O)O)Cl)=O Chemical compound C(C(C)C(C(=O)O)Cl)=O NVVNISHGUAJVFR-UHFFFAOYSA-N 0.000 description 1
- MPWOLTQAJKMONO-UHFFFAOYSA-N CCN(CC)CC.NC(SC(C=C1)=NC=C1Cl)=S Chemical compound CCN(CC)CC.NC(SC(C=C1)=NC=C1Cl)=S MPWOLTQAJKMONO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- HQGBWUXEXCCXBU-UHFFFAOYSA-N N,N-diethylethanamine hypobromous acid Chemical compound BrO.CCN(CC)CC HQGBWUXEXCCXBU-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002152 aqueous-organic solution Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-O ethylaminium Chemical compound CC[NH3+] QUSNBJAOOMFDIB-UHFFFAOYSA-O 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 125000005283 haloketone group Chemical group 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- AOWIKWNIPGIZGG-UHFFFAOYSA-N methyl 4-bromo-5-oxohexanoate Chemical compound COC(=O)CCC(Br)C(C)=O AOWIKWNIPGIZGG-UHFFFAOYSA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- IHJWFFDXQRAIJG-UHFFFAOYSA-N pyridin-2-yl carbamodithioate Chemical compound C(N)(SC1=NC=CC=C1)=S IHJWFFDXQRAIJG-UHFFFAOYSA-N 0.000 description 1
- KXLNMMHHVYWLIS-UHFFFAOYSA-N pyridin-3-ylcarbamodithioic acid Chemical compound SC(=S)NC1=CC=CN=C1 KXLNMMHHVYWLIS-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7715072A FR2391212A1 (fr) | 1977-05-17 | 1977-05-17 | Nouveaux derives de la thiazolidine, leur preparation et les compositions qui les contiennent |
| FR7812185A FR2424269A2 (fr) | 1978-04-25 | 1978-04-25 | Nouveaux derives de la thiazolidine, leur preparation et les compositions qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU852171A3 true SU852171A3 (ru) | 1981-07-30 |
Family
ID=26220024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782615706A SU852171A3 (ru) | 1977-05-17 | 1978-05-17 | Способ получени производных ОКСиТиАзОлидиНТиОКЕТОНА или иХ СОлЕй |
Country Status (17)
| Country | Link |
|---|---|
| AT (1) | ATA356778A (fr) |
| AU (1) | AU3613778A (fr) |
| BE (1) | BE867128A (fr) |
| CA (1) | CA1093078A (fr) |
| DE (1) | DE2821555A1 (fr) |
| DK (1) | DK214078A (fr) |
| ES (1) | ES469883A1 (fr) |
| GB (1) | GB1586917A (fr) |
| IE (1) | IE46829B1 (fr) |
| IL (1) | IL54735A0 (fr) |
| IT (1) | IT1096219B (fr) |
| LU (1) | LU79663A1 (fr) |
| NZ (1) | NZ187290A (fr) |
| OA (1) | OA05950A (fr) |
| PT (1) | PT68047B (fr) |
| SE (1) | SE7805589L (fr) |
| SU (1) | SU852171A3 (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2464954A2 (fr) * | 1979-09-12 | 1981-03-20 | Rhone Poulenc Ind | Nouveaux derives de la thiazolidine, leur preparation et les compositions qui les contiennent |
-
1978
- 1978-04-27 OA OA56480BISA patent/OA05950A/fr unknown
- 1978-05-16 IT IT23473/78A patent/IT1096219B/it active
- 1978-05-16 NZ NZ187290A patent/NZ187290A/xx unknown
- 1978-05-16 GB GB19926/78A patent/GB1586917A/en not_active Expired
- 1978-05-16 IE IE983/78A patent/IE46829B1/en unknown
- 1978-05-16 DK DK214078A patent/DK214078A/da unknown
- 1978-05-16 ES ES469883A patent/ES469883A1/es not_active Expired
- 1978-05-16 SE SE7805589A patent/SE7805589L/xx unknown
- 1978-05-16 IL IL54735A patent/IL54735A0/xx unknown
- 1978-05-16 PT PT197868047A patent/PT68047B/fr unknown
- 1978-05-16 AU AU36137/78A patent/AU3613778A/en active Pending
- 1978-05-16 LU LU79663A patent/LU79663A1/fr unknown
- 1978-05-16 BE BE187744A patent/BE867128A/fr unknown
- 1978-05-17 SU SU782615706A patent/SU852171A3/ru active
- 1978-05-17 CA CA303,554A patent/CA1093078A/fr not_active Expired
- 1978-05-17 AT AT356778A patent/ATA356778A/de not_active IP Right Cessation
- 1978-05-17 DE DE19782821555 patent/DE2821555A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| PT68047B (fr) | 1979-09-28 |
| SE7805589L (sv) | 1978-11-18 |
| DE2821555A1 (de) | 1978-11-30 |
| ATA356778A (de) | 1981-01-15 |
| NZ187290A (en) | 1981-04-24 |
| BE867128A (fr) | 1978-11-16 |
| LU79663A1 (fr) | 1979-02-02 |
| IE780983L (en) | 1978-11-17 |
| CA1093078A (fr) | 1981-01-06 |
| IL54735A0 (en) | 1978-07-31 |
| AU3613778A (en) | 1979-11-22 |
| GB1586917A (en) | 1981-03-25 |
| IE46829B1 (en) | 1983-10-05 |
| IT7823473A0 (it) | 1978-05-16 |
| OA05950A (fr) | 1981-06-30 |
| ES469883A1 (es) | 1979-09-16 |
| PT68047A (fr) | 1978-06-01 |
| IT1096219B (it) | 1985-08-26 |
| DK214078A (da) | 1978-11-18 |
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