NL7908189A - Nieuwe perhydrothiazine-1.3-derivaten, de bereiding ervan, alsmede geneesmiddelen die de nieuwe derivaten bevatten. - Google Patents
Nieuwe perhydrothiazine-1.3-derivaten, de bereiding ervan, alsmede geneesmiddelen die de nieuwe derivaten bevatten. Download PDFInfo
- Publication number
- NL7908189A NL7908189A NL7908189A NL7908189A NL7908189A NL 7908189 A NL7908189 A NL 7908189A NL 7908189 A NL7908189 A NL 7908189A NL 7908189 A NL7908189 A NL 7908189A NL 7908189 A NL7908189 A NL 7908189A
- Authority
- NL
- Netherlands
- Prior art keywords
- general formula
- derivative
- preparation
- perhydrothiazine
- symbols
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 15
- 229940126601 medicinal product Drugs 0.000 title 1
- 239000012990 dithiocarbamate Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 125000005999 2-bromoethyl group Chemical group 0.000 claims description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 150000004897 thiazines Chemical class 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 78
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- -1 3-oxobutyl- (5-chloro-2-pyridyl) dithiocarbamate Chemical compound 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000012153 distilled water Substances 0.000 description 10
- 239000000155 melt Substances 0.000 description 10
- 239000000377 silicon dioxide Substances 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- 239000013078 crystal Substances 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 238000010828 elution Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
- 238000002329 infrared spectrum Methods 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-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 6
- 235000019271 petrolatum Nutrition 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 239000004264 Petrolatum Substances 0.000 description 5
- 229940066842 petrolatum Drugs 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 241000244206 Nematoda Species 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 229940099259 vaseline Drugs 0.000 description 3
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 201000006353 Filariasis Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 230000000507 anthelmentic effect Effects 0.000 description 2
- 229940124339 anthelmintic agent Drugs 0.000 description 2
- 239000000921 anthelmintic agent Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- CURCMGVZNYCRNY-UHFFFAOYSA-N trimethylazanium;iodide Chemical compound I.CN(C)C CURCMGVZNYCRNY-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- BEGGKYJGVPGIES-UHFFFAOYSA-N C(N)(SC1=NC=CC=C1)=S.C(C)N(CC)CC Chemical compound C(N)(SC1=NC=CC=C1)=S.C(C)N(CC)CC BEGGKYJGVPGIES-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000243780 Heligmosomoides polygyrus Species 0.000 description 1
- 208000006968 Helminthiasis Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000243994 Litomosoides carinii Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000144290 Sigmodon hispidus Species 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 208000008576 dracunculiasis Diseases 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000001926 lymphatic effect Effects 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000829 suppository 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7832387A FR2441626A1 (fr) | 1978-11-16 | 1978-11-16 | Nouveaux derives de la perhydrothiazine-1,3 leur preparation et les medicaments qui les contiennent |
| FR7832387 | 1978-11-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL7908189A true NL7908189A (nl) | 1980-05-20 |
Family
ID=9214965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL7908189A NL7908189A (nl) | 1978-11-16 | 1979-11-08 | Nieuwe perhydrothiazine-1.3-derivaten, de bereiding ervan, alsmede geneesmiddelen die de nieuwe derivaten bevatten. |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4271156A (fr) |
| JP (1) | JPS5572187A (fr) |
| AT (1) | ATA727679A (fr) |
| AU (1) | AU5278479A (fr) |
| BE (1) | BE880096A (fr) |
| DE (1) | DE2946409A1 (fr) |
| DK (1) | DK485179A (fr) |
| ES (1) | ES485990A1 (fr) |
| FR (1) | FR2441626A1 (fr) |
| GB (1) | GB2037749A (fr) |
| IL (1) | IL58728A0 (fr) |
| IT (1) | IT1127241B (fr) |
| LU (1) | LU81895A1 (fr) |
| NL (1) | NL7908189A (fr) |
| NZ (1) | NZ192119A (fr) |
| OA (1) | OA06370A (fr) |
| PH (1) | PH14654A (fr) |
| PT (1) | PT70438A (fr) |
| SE (1) | SE7909440L (fr) |
| SU (1) | SU858565A3 (fr) |
| ZA (1) | ZA796122B (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1987006230A1 (fr) * | 1986-04-10 | 1987-10-22 | Leo Pharmaceutical Products Ltd. A/S | Procede servant a preparer des derives d'acide penicillanique |
| CN102234271B (zh) * | 2010-04-21 | 2015-06-10 | 北京大学 | 芳杂(烷基)氨基二硫代甲酸酯类化合物、其制备方法和应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2789114A (en) * | 1955-10-28 | 1957-04-16 | Dow Chemical Co | Triethylamine salt of nu-(2-pyridyl)-dithiocarbamic acid |
| US2909460A (en) * | 1957-03-21 | 1959-10-20 | Monsanto Chemicals | 3-amino-2, 3-dihydro-1, 3-thiazine-2-thiones and process of inhibiting fungus growth |
| US3726880A (en) * | 1971-09-07 | 1973-04-10 | Parke Davis & Co | Organic amides and methods for their production |
| US3732216A (en) * | 1971-11-17 | 1973-05-08 | Smith Kline French Lab | 3-heteroaryl-2-thio-1,3-thiazane-2,4-diones |
| NL7804971A (nl) * | 1977-05-17 | 1978-11-21 | Rhone Poulenc Ind | Nieuwe 4-hydroxythiazolidinethion-2-derivaten, de be- reiding ervan en preparaten, die de nieuwe derivaten bevatten. |
-
1978
- 1978-11-16 FR FR7832387A patent/FR2441626A1/fr active Pending
-
1979
- 1979-11-01 OA OA56930A patent/OA06370A/fr unknown
- 1979-11-08 NL NL7908189A patent/NL7908189A/nl not_active Application Discontinuation
- 1979-11-12 PT PT70438A patent/PT70438A/fr unknown
- 1979-11-14 GB GB7939432A patent/GB2037749A/en not_active Withdrawn
- 1979-11-14 JP JP14663079A patent/JPS5572187A/ja active Pending
- 1979-11-14 NZ NZ192119A patent/NZ192119A/xx unknown
- 1979-11-14 ZA ZA00796122A patent/ZA796122B/xx unknown
- 1979-11-14 AT AT0727679A patent/ATA727679A/de unknown
- 1979-11-14 US US06/094,335 patent/US4271156A/en not_active Expired - Lifetime
- 1979-11-14 PH PH23279A patent/PH14654A/en unknown
- 1979-11-14 AU AU52784/79A patent/AU5278479A/en not_active Abandoned
- 1979-11-15 DK DK485179A patent/DK485179A/da unknown
- 1979-11-15 ES ES485990A patent/ES485990A1/es not_active Expired
- 1979-11-15 SE SE7909440A patent/SE7909440L/xx unknown
- 1979-11-15 LU LU81895A patent/LU81895A1/fr unknown
- 1979-11-15 IL IL58728A patent/IL58728A0/xx unknown
- 1979-11-15 SU SU792841756A patent/SU858565A3/ru active
- 1979-11-16 DE DE19792946409 patent/DE2946409A1/de not_active Withdrawn
- 1979-11-16 IT IT27343/79A patent/IT1127241B/it active
- 1979-11-16 BE BE0/198160A patent/BE880096A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2441626A1 (fr) | 1980-06-13 |
| ZA796122B (en) | 1980-11-26 |
| AU5278479A (en) | 1980-05-22 |
| DK485179A (da) | 1980-05-17 |
| JPS5572187A (en) | 1980-05-30 |
| LU81895A1 (fr) | 1980-06-05 |
| IT1127241B (it) | 1986-05-21 |
| NZ192119A (en) | 1981-12-15 |
| SE7909440L (sv) | 1980-05-17 |
| ATA727679A (de) | 1983-05-15 |
| PH14654A (en) | 1981-10-14 |
| BE880096A (fr) | 1980-05-16 |
| ES485990A1 (es) | 1980-05-16 |
| GB2037749A (en) | 1980-07-16 |
| OA06370A (fr) | 1981-08-31 |
| IL58728A0 (en) | 1980-02-29 |
| US4271156A (en) | 1981-06-02 |
| IT7927343A0 (it) | 1979-11-16 |
| PT70438A (fr) | 1979-12-01 |
| DE2946409A1 (de) | 1980-05-29 |
| SU858565A3 (ru) | 1981-08-23 |
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