FR2509303A1 - Derives de l'acide 1,4-thiazane-carboxylique, leurs preparation et utilisation ainsi que les compositions contenant ces derives - Google Patents
Derives de l'acide 1,4-thiazane-carboxylique, leurs preparation et utilisation ainsi que les compositions contenant ces derives Download PDFInfo
- Publication number
- FR2509303A1 FR2509303A1 FR8207461A FR8207461A FR2509303A1 FR 2509303 A1 FR2509303 A1 FR 2509303A1 FR 8207461 A FR8207461 A FR 8207461A FR 8207461 A FR8207461 A FR 8207461A FR 2509303 A1 FR2509303 A1 FR 2509303A1
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- FR
- France
- Prior art keywords
- group
- linear
- formula
- derivative
- thiazane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- 239000000203 mixture Substances 0.000 title claims description 42
- 238000002360 preparation method Methods 0.000 title claims description 9
- -1 PHENYL CORE Chemical group 0.000 claims abstract description 66
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
- 239000001257 hydrogen Substances 0.000 claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 7
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract description 5
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims abstract 3
- 229940091173 hydantoin Drugs 0.000 claims abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 88
- 239000000243 solution Substances 0.000 claims description 56
- 239000002253 acid Substances 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 36
- 230000002829 reductive effect Effects 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 230000008569 process Effects 0.000 claims description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 239000002609 medium Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 230000009467 reduction Effects 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 230000003647 oxidation Effects 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 238000007363 ring formation reaction Methods 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 6
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 230000010933 acylation Effects 0.000 claims description 4
- 238000005917 acylation reaction Methods 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 230000032050 esterification Effects 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000006188 syrup Substances 0.000 claims description 4
- 235000020357 syrup Nutrition 0.000 claims description 4
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 4
- QEQYAQFYVFRGQD-YFKPBYRVSA-N (2s)-2-amino-5-[[methyl(nitroso)carbamoyl]amino]pentanoic acid Chemical compound O=NN(C)C(=O)NCCC[C@H](N)C(O)=O QEQYAQFYVFRGQD-YFKPBYRVSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 claims description 2
- 235000019483 Peanut oil Nutrition 0.000 claims description 2
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims description 2
- 208000007536 Thrombosis Diseases 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 238000007098 aminolysis reaction Methods 0.000 claims description 2
- 239000000908 ammonium hydroxide Substances 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 150000001944 cysteine derivatives Chemical class 0.000 claims description 2
- 238000011161 development Methods 0.000 claims description 2
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 claims description 2
- 229940093471 ethyl oleate Drugs 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000000312 peanut oil Substances 0.000 claims description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
- 108090000623 proteins and genes Proteins 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 101150084750 1 gene Proteins 0.000 claims 1
- MSTFRUQNYRRUKZ-UHFFFAOYSA-N 5,6-dihydro-2h-thiazine Chemical class C1CC=CNS1 MSTFRUQNYRRUKZ-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 238000006136 alcoholysis reaction Methods 0.000 claims 1
- 230000009435 amidation Effects 0.000 claims 1
- 238000007112 amidation reaction Methods 0.000 claims 1
- 239000008298 dragée Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 229910001415 sodium ion Inorganic materials 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- JOKIQGQOKXGHDV-UHFFFAOYSA-N thiomorpholine-3-carboxylic acid Chemical class [O-]C(=O)C1CSCC[NH2+]1 JOKIQGQOKXGHDV-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 abstract 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical group [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 87
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 66
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 48
- 239000000047 product Substances 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
- 235000019441 ethanol Nutrition 0.000 description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 25
- 239000002904 solvent Substances 0.000 description 25
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/12—1,4-Thiazines; Hydrogenated 1,4-thiazines not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/16—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Hematology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Facsimiles In General (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU83327A LU83327A1 (fr) | 1981-04-29 | 1981-04-29 | Procede de preparation de derives de 1,4-thiazine,leur utilisation ainsi que compositions contenant ces derives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2509303A1 true FR2509303A1 (fr) | 1983-01-14 |
Family
ID=19729637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8207461A Withdrawn FR2509303A1 (fr) | 1981-04-29 | 1982-04-29 | Derives de l'acide 1,4-thiazane-carboxylique, leurs preparation et utilisation ainsi que les compositions contenant ces derives |
Country Status (16)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2618434A1 (fr) * | 1987-07-21 | 1989-01-27 | Oreal | Esters d'acide thiamorpholinone carboxylique et de ses derives, leur procede de preparation et leur utilisation dans le domaine cosmetique et dermo-pharmaceutique |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3436386A1 (de) * | 1984-10-04 | 1986-04-10 | Merck Patent Gmbh, 6100 Darmstadt | (thio)morpholine |
| AU4750990A (en) * | 1988-12-14 | 1990-07-10 | Hicks, Richard | Method for predicting biological activity of antibiotics, and novel non beta-lactam antibacterial agents derived therefrom |
| DK2809669T3 (da) | 2012-02-03 | 2017-05-01 | Sanofi Sa | Kondenserede pyrroldicarboxamider og deres anvendelse som farmaceutika |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2187327A1 (enrdf_load_stackoverflow) * | 1972-06-15 | 1974-01-18 | Rech Pharm Scientifiques | |
| US4179276A (en) * | 1977-02-01 | 1979-12-18 | E. I. Du Pont De Nemours And Company | Novel imidazothiazine-1,3 (2H)-diones |
| JPS5540658A (en) * | 1978-09-19 | 1980-03-22 | Tanabe Seiyaku Co Ltd | 1,4-thiazan-3-carboxylic ester derivative and its preparation |
-
1981
- 1981-04-29 LU LU83327A patent/LU83327A1/fr unknown
-
1982
- 1982-04-21 WO PCT/BE1982/000009 patent/WO1982003860A1/en active IP Right Grant
- 1982-04-21 JP JP57501451A patent/JPS58500713A/ja active Granted
- 1982-04-21 GB GB08235353A patent/GB2111056B/en not_active Expired
- 1982-04-21 NL NL8220153A patent/NL8220153A/nl unknown
- 1982-04-28 ES ES82511759A patent/ES8307233A1/es not_active Expired
- 1982-04-28 PT PT74813A patent/PT74813B/pt unknown
- 1982-04-29 IT IT20998/82A patent/IT1190794B/it active
- 1982-04-29 FR FR8207461A patent/FR2509303A1/fr not_active Withdrawn
- 1982-04-29 GR GR68018A patent/GR75996B/el unknown
- 1982-04-29 BE BE0/207967A patent/BE893025A/fr not_active IP Right Cessation
- 1982-04-29 ZA ZA822926A patent/ZA822926B/xx unknown
- 1982-04-29 KR KR1019820001874A patent/KR830010089A/ko not_active Ceased
- 1982-12-14 FI FI771226A patent/FI66366C/fi not_active IP Right Cessation
- 1982-12-21 SE SE8207294A patent/SE8207294L/xx not_active Application Discontinuation
- 1982-12-28 NO NO824398A patent/NO824398L/no unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2187327A1 (enrdf_load_stackoverflow) * | 1972-06-15 | 1974-01-18 | Rech Pharm Scientifiques | |
| US4179276A (en) * | 1977-02-01 | 1979-12-18 | E. I. Du Pont De Nemours And Company | Novel imidazothiazine-1,3 (2H)-diones |
| JPS5540658A (en) * | 1978-09-19 | 1980-03-22 | Tanabe Seiyaku Co Ltd | 1,4-thiazan-3-carboxylic ester derivative and its preparation |
Non-Patent Citations (4)
| Title |
|---|
| CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 29, no. 6, juin 1981, pages 1554-1560; KAZUO SAKAI et al.: "Convenient Synthesis of 1,4-Thiazane-3-carboxylic Acid Derivatives" * |
| CHEMICAL ABSTRACTS, vol. 93, no. 21, 24 novembre 1980, page 693, no. 204671z, Columbus, Ohio, US; & JP - A - 80 40 658 (TANABE SEIYAKU CO., LTD.) 22-03-1980 * |
| JOURNAL OF THE CHEMICAL SOCIETY, Perkin Transactions I, no. 11, 1976, pages 1195-1199; J.F. CARSON et al.: "Cyclization of (+)- and (-)-S-(2-Methylprop-1-enyl)-L-cysteine S-Oxides" * |
| THE JOURNAL OF ORGANIC CHEMISTRY, vol. 34, no. 6, juin 1969, pages 1996-1998; J.F. CARSON et al.: "The Base Cyclization of trans-S-(1-Butenyl)-L-cysteine S-oxide" * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2618434A1 (fr) * | 1987-07-21 | 1989-01-27 | Oreal | Esters d'acide thiamorpholinone carboxylique et de ses derives, leur procede de preparation et leur utilisation dans le domaine cosmetique et dermo-pharmaceutique |
| BE1006721A3 (fr) * | 1987-07-21 | 1994-11-29 | Oreal | Esters d'acide thiamorpholine carboxylique et de ses derives, leur procede de preparation et leur utilisation dans le domaine cosmetique et dermopharmaceutique. |
Also Published As
| Publication number | Publication date |
|---|---|
| ES511759A0 (es) | 1983-07-01 |
| GB2111056B (en) | 1985-03-06 |
| GR75996B (enrdf_load_stackoverflow) | 1984-08-03 |
| PT74813B (fr) | 1983-10-26 |
| SE8207294D0 (sv) | 1982-12-21 |
| KR830010089A (ko) | 1983-12-26 |
| LU83327A1 (fr) | 1983-03-24 |
| IT1190794B (it) | 1988-02-24 |
| ES8307233A1 (es) | 1983-07-01 |
| JPH0330592B2 (enrdf_load_stackoverflow) | 1991-04-30 |
| IT8220998A0 (it) | 1982-04-29 |
| NO824398L (no) | 1982-12-28 |
| FI66366C (fi) | 1984-10-10 |
| FI66366B (fi) | 1984-06-29 |
| NL8220153A (nl) | 1983-03-01 |
| FI824279L (fi) | 1982-12-14 |
| JPS58500713A (ja) | 1983-05-06 |
| PT74813A (fr) | 1982-05-01 |
| SE8207294L (sv) | 1982-12-21 |
| GB2111056A (en) | 1983-06-29 |
| BE893025A (fr) | 1982-10-29 |
| WO1982003860A1 (en) | 1982-11-11 |
| ZA822926B (en) | 1983-03-30 |
| FI824279A0 (fi) | 1982-12-14 |
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| TP | Transmission of property | ||
| TP | Transmission of property | ||
| RE | Withdrawal of published application |