LT3054B - 3- and 5-substituted 1,2,3,4-oxatriazole-5-imine compounds, a process for the preparation thereof, a pharmaceutical preparation containing said compounds and the use of said compounds for the preparation of medicaments - Google Patents
3- and 5-substituted 1,2,3,4-oxatriazole-5-imine compounds, a process for the preparation thereof, a pharmaceutical preparation containing said compounds and the use of said compounds for the preparation of medicaments Download PDFInfo
- Publication number
- LT3054B LT3054B LTIP816A LTIP816A LT3054B LT 3054 B LT3054 B LT 3054B LT IP816 A LTIP816 A LT IP816A LT IP816 A LTIP816 A LT IP816A LT 3054 B LT3054 B LT 3054B
- Authority
- LT
- Lithuania
- Prior art keywords
- compounds
- alkyl
- oxatriazole
- imine
- aryl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 48
- QPTISOPQFLIZCY-UHFFFAOYSA-N oxatriazol-5-amine Chemical class NC1=NN=NO1 QPTISOPQFLIZCY-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 238000002360 preparation method Methods 0.000 title claims description 10
- 239000003814 drug Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 4
- 230000008569 process Effects 0.000 title claims description 3
- -1 nitro, cyano, phenyl Chemical group 0.000 claims abstract description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 230000002378 acidificating effect Effects 0.000 claims abstract description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000002466 imines Chemical class 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 230000001088 anti-asthma Effects 0.000 claims 1
- 239000000924 antiasthmatic agent Substances 0.000 claims 1
- 235000008216 herbs Nutrition 0.000 claims 1
- 201000001881 impotence Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 201000011461 pre-eclampsia Diseases 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- 239000000203 mixture Substances 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 238000003756 stirring Methods 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 239000000047 product Substances 0.000 description 18
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 238000001914 filtration Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 239000001569 carbon dioxide Substances 0.000 description 8
- 229910002092 carbon dioxide Inorganic materials 0.000 description 8
- 210000000056 organ Anatomy 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 230000004071 biological effect Effects 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- NCGICGYLBXGBGN-UHFFFAOYSA-N 3-morpholin-4-yl-1-oxa-3-azonia-2-azanidacyclopent-3-en-5-imine;hydrochloride Chemical compound Cl.[N-]1OC(=N)C=[N+]1N1CCOCC1 NCGICGYLBXGBGN-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VIMSYKAYPLTMSQ-UHFFFAOYSA-N ClC=1C(=C(C=CC1)N1NOC=N1)C Chemical compound ClC=1C(=C(C=CC1)N1NOC=N1)C VIMSYKAYPLTMSQ-UHFFFAOYSA-N 0.000 description 4
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000008602 contraction Effects 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 210000003437 trachea Anatomy 0.000 description 4
- VPJXQGSRWJZDOB-UHFFFAOYSA-O 2-carbamoyloxyethyl(trimethyl)azanium Chemical compound C[N+](C)(C)CCOC(N)=O VPJXQGSRWJZDOB-UHFFFAOYSA-O 0.000 description 3
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 3
- QQZWEECEMNQSTG-UHFFFAOYSA-N Ethyl nitrite Chemical compound CCON=O QQZWEECEMNQSTG-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 208000006673 asthma Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 2
- 239000000006 Nitroglycerin Substances 0.000 description 2
- 208000007536 Thrombosis Diseases 0.000 description 2
- 125000005233 alkylalcohol group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- XEYBHCRIKKKOSS-UHFFFAOYSA-N disodium;azanylidyneoxidanium;iron(2+);pentacyanide Chemical compound [Na+].[Na+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].[O+]#N XEYBHCRIKKKOSS-UHFFFAOYSA-N 0.000 description 2
- 229960003711 glyceryl trinitrate Drugs 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 238000012417 linear regression Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000012925 reference material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 229940083618 sodium nitroprusside Drugs 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- UGFVODHLEUQXMH-UHFFFAOYSA-N (3-chloro-2-methylanilino)thiourea Chemical compound CC1=C(Cl)C=CC=C1NNC(N)=S UGFVODHLEUQXMH-UHFFFAOYSA-N 0.000 description 1
- NFVOTDWJCRXNTA-UHFFFAOYSA-N (3-chloro-2-methylphenyl)hydrazine;hydrochloride Chemical compound Cl.CC1=C(Cl)C=CC=C1NN NFVOTDWJCRXNTA-UHFFFAOYSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- QFGLIIGBBQLMOS-UHFFFAOYSA-N 3-(3-chloro-2-methylphenyl)-2h-oxatriazol-2-ium-5-amine;chloride Chemical compound Cl.CC1=C(Cl)C=CC=C1N1NC(=N)ON1 QFGLIIGBBQLMOS-UHFFFAOYSA-N 0.000 description 1
- DZMNKFGBWZJKRP-UHFFFAOYSA-N 3-phenyl-2h-oxatriazol-5-amine Chemical class N1OC(=N)NN1C1=CC=CC=C1 DZMNKFGBWZJKRP-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- IVRSSZQMLHNCKE-UHFFFAOYSA-N Cl.O1NN=NC1=N Chemical compound Cl.O1NN=NC1=N IVRSSZQMLHNCKE-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 101100341037 Drosophila melanogaster Inx7 gene Proteins 0.000 description 1
- 235000006679 Mentha X verticillata Nutrition 0.000 description 1
- 235000002899 Mentha suaveolens Nutrition 0.000 description 1
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910001963 alkali metal nitrate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000702 anti-platelet effect Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- UBAZGMLMVVQSCD-UHFFFAOYSA-N carbon dioxide;molecular oxygen Chemical compound O=O.O=C=O UBAZGMLMVVQSCD-UHFFFAOYSA-N 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- DUVOZUPPHBRJJO-UHFFFAOYSA-N ethyl 2-isocyanatoacetate Chemical compound CCOC(=O)CN=C=O DUVOZUPPHBRJJO-UHFFFAOYSA-N 0.000 description 1
- XBSGYVHOINMTIM-UHFFFAOYSA-N ethyl 3-isocyanatopropanoate Chemical compound CCOC(=O)CCN=C=O XBSGYVHOINMTIM-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- XLFWDASMENKTKL-UHFFFAOYSA-N molsidomine Chemical compound O1C(N=C([O-])OCC)=C[N+](N2CCOCC2)=N1 XLFWDASMENKTKL-UHFFFAOYSA-N 0.000 description 1
- 229960004027 molsidomine Drugs 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical compound O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 231100000194 ovacidal Toxicity 0.000 description 1
- 230000003151 ovacidal effect Effects 0.000 description 1
- CQDAMYNQINDRQC-UHFFFAOYSA-N oxatriazole Chemical group C1=NN=NO1 CQDAMYNQINDRQC-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 230000003578 releasing effect Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 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
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 150000003583 thiosemicarbazides Chemical class 0.000 description 1
- 230000002541 vasodepressive effect Effects 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- ZHYMSIKIWUMEMF-UHFFFAOYSA-N yttrium hydrochloride Chemical compound Cl.[Y] ZHYMSIKIWUMEMF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK921003A DK100392D0 (da) | 1992-08-10 | 1992-08-10 | 3- og 5-substituerede 1,2,3,4-oxatriazol-5-iminforbindelser og fremgangsmaade til fremstilling deraf, farmaceutisk praeparat indeholdende disse forbindelser samt forbindelsernes anvendelse til fremstilling af laegemidler |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LTIP816A LTIP816A (en) | 1994-05-15 |
| LT3054B true LT3054B (en) | 1994-10-25 |
Family
ID=8099920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTIP816A LT3054B (en) | 1992-08-10 | 1993-07-23 | 3- and 5-substituted 1,2,3,4-oxatriazole-5-imine compounds, a process for the preparation thereof, a pharmaceutical preparation containing said compounds and the use of said compounds for the preparation of medicaments |
Country Status (29)
| Country | Link |
|---|---|
| EP (1) | EP0654028B1 (de) |
| JP (1) | JPH07509703A (de) |
| CN (1) | CN1086813A (de) |
| AP (1) | AP455A (de) |
| AT (1) | ATE136893T1 (de) |
| AU (1) | AU4418193A (de) |
| BG (1) | BG99378A (de) |
| BR (1) | BR9306880A (de) |
| CA (1) | CA2140641A1 (de) |
| CZ (1) | CZ33995A3 (de) |
| DE (1) | DE69302279T2 (de) |
| DK (2) | DK100392D0 (de) |
| EE (1) | EE9400084A (de) |
| ES (1) | ES2085787T3 (de) |
| FI (1) | FI950575A7 (de) |
| GR (1) | GR3019681T3 (de) |
| HU (1) | HUT71230A (de) |
| IS (1) | IS4052A (de) |
| LT (1) | LT3054B (de) |
| LV (1) | LV10263B (de) |
| MX (1) | MX9304788A (de) |
| NZ (1) | NZ253681A (de) |
| OA (1) | OA10127A (de) |
| PL (1) | PL307395A1 (de) |
| RU (1) | RU95106464A (de) |
| SI (1) | SI9300425A (de) |
| SK (1) | SK18295A3 (de) |
| WO (1) | WO1994003442A1 (de) |
| ZA (1) | ZA935199B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU8057194A (en) * | 1994-10-07 | 1996-05-02 | A/S Gea Farmaceutisk Fabrik | Substituted 3-phenyl-1,2,3,4-oxatriazole-5-imines useful for the treatment of asthma and thrombosis |
| US6399618B1 (en) | 1997-07-09 | 2002-06-04 | Cardiome Pharma Corp | Compositions and methods for modulating sexual activity |
| FR2786699B1 (fr) * | 1998-12-02 | 2002-10-04 | Philippe Gorny | Medicament destine notamment a prevenir ou traiter les dysfonctions sexuelles |
| CN111217817B (zh) * | 2020-02-26 | 2022-06-10 | 山东潍坊润丰化工股份有限公司 | 一种三唑并嘧啶类除草剂的制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2015878A (en) | 1978-03-10 | 1979-09-19 | Shell Int Research | Biocidal compositions |
| US4329355A (en) | 1979-03-01 | 1982-05-11 | Henry David W | Mesoionic antitumor compositions and methods for using the same in the treatment of cancer |
-
1992
- 1992-08-10 DK DK921003A patent/DK100392D0/da not_active Application Discontinuation
-
1993
- 1993-07-08 DE DE69302279T patent/DE69302279T2/de not_active Expired - Fee Related
- 1993-07-08 EP EP93914656A patent/EP0654028B1/de not_active Expired - Lifetime
- 1993-07-08 BR BR9306880A patent/BR9306880A/pt not_active Application Discontinuation
- 1993-07-08 AU AU44181/93A patent/AU4418193A/en not_active Abandoned
- 1993-07-08 DK DK93914656.9T patent/DK0654028T3/da active
- 1993-07-08 CA CA002140641A patent/CA2140641A1/en not_active Abandoned
- 1993-07-08 AT AT93914656T patent/ATE136893T1/de active
- 1993-07-08 HU HU9500401A patent/HUT71230A/hu unknown
- 1993-07-08 RU RU95106464/04A patent/RU95106464A/ru unknown
- 1993-07-08 SK SK182-95A patent/SK18295A3/sk unknown
- 1993-07-08 ES ES93914656T patent/ES2085787T3/es not_active Expired - Lifetime
- 1993-07-08 WO PCT/DK1993/000234 patent/WO1994003442A1/en not_active Ceased
- 1993-07-08 NZ NZ253681A patent/NZ253681A/en unknown
- 1993-07-08 JP JP6504904A patent/JPH07509703A/ja active Pending
- 1993-07-08 PL PL93307395A patent/PL307395A1/xx unknown
- 1993-07-08 CZ CZ95339A patent/CZ33995A3/cs unknown
- 1993-07-13 IS IS4052A patent/IS4052A/is unknown
- 1993-07-19 ZA ZA935199A patent/ZA935199B/xx unknown
- 1993-07-23 LT LTIP816A patent/LT3054B/lt not_active IP Right Cessation
- 1993-07-26 AP APAP/P/1993/000559A patent/AP455A/en active
- 1993-08-06 MX MX9304788A patent/MX9304788A/es not_active Application Discontinuation
- 1993-08-10 SI SI9300425A patent/SI9300425A/sl unknown
- 1993-08-10 LV LVP-93-1027A patent/LV10263B/en unknown
- 1993-08-10 CN CN93109277A patent/CN1086813A/zh active Pending
-
1994
- 1994-08-09 EE EE9400084A patent/EE9400084A/xx unknown
-
1995
- 1995-01-27 BG BG99378A patent/BG99378A/bg unknown
- 1995-02-09 FI FI950575A patent/FI950575A7/fi not_active Application Discontinuation
- 1995-02-10 OA OA60609A patent/OA10127A/en unknown
-
1996
- 1996-04-19 GR GR960401060T patent/GR3019681T3/el unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2015878A (en) | 1978-03-10 | 1979-09-19 | Shell Int Research | Biocidal compositions |
| US4329355A (en) | 1979-03-01 | 1982-05-11 | Henry David W | Mesoionic antitumor compositions and methods for using the same in the treatment of cancer |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6060139B2 (ja) | 新規で生理学的に有用なニトロキシル供与体としてのｎ−ヒドロキシルスルホンアミド誘導体 | |
| JP6122163B2 (ja) | 新規で生理学的に有用なニトロキシル供与体としてのｎ−ヒドロキシルスルホンアミド誘導体 | |
| Lin et al. | New synthesis of isoxazoles and isothiazoles. A convenient synthesis of thioenaminones from enaminones | |
| DK173703B1 (da) | Fremgangsmåder til fremstilling af henholdsvis D,L-(threo)- og D-(treo)-1-aryl-2-acylamido-3-fluor-1-propanoler | |
| AU8047598A (en) | New thiazolidinedione, oxazolidinedione and oxadiazolidinedione derivatives | |
| LT3054B (en) | 3- and 5-substituted 1,2,3,4-oxatriazole-5-imine compounds, a process for the preparation thereof, a pharmaceutical preparation containing said compounds and the use of said compounds for the preparation of medicaments | |
| CN102690241B (zh) | 含异噁唑啉结构的苯甲酰脲类化合物及制备和应用 | |
| CN103965182A (zh) | 制备含1,3,4-噁二唑的吡唑类化合物用于治疗肿瘤的药物 | |
| SI9210142A (en) | 3-substituted 1,2,3,4-oxitriazole-5-imin compounds, procedure for their preparation and preparations comprising them | |
| HU177039B (hu) | Sposob poluchenija al'fa-aril-omega,omega,omega-triftoro-alkil-aminov | |
| JPS6012348B2 (ja) | ハロゲン化カルバモイル化合物 | |
| CA2357450A1 (en) | Phenoxazine analogs useful as amyloid aggregation inhibitors and treatment of alzheimer's disease and disorders related to amyloidosis | |
| JPH09169747A (ja) | 新規置換フェニルチアゾリジン−２，４−ジオン誘導体及びその製造法 | |
| Duggan et al. | Ring expansion reactions of 4-amino-1, 1-dioxo-[1, 2, 3, 5]-thiatriazoles | |
| DK154210B (da) | Analogifremgangsmaade til fremstilling af 2-methoxyphenylestere af n-substituerede aminosyrer | |
| KR100218196B1 (ko) | 2-아미노티아졸 카르복사미드 유도체의 제조방법 | |
| CN119119019A (zh) | 一种杂环磺酰胺/磺酸酯衍生物及其制备方法、应用 | |
| JPS6025430B2 (ja) | 新規なモルホリン誘導体の製造法 | |
| JPS59204156A (ja) | 新規アシル化剤によるアシル化方法 | |
| JP2000109459A (ja) | アリールビニルスルホン溶液 | |
| CN107759561A (zh) | 一种具有杀虫活性的邻甲酰氨基苯甲酰胺类化合物及其应用 | |
| CN103319434A (zh) | 3-氨基-7-二烷基胺基取代吩噻嗪类化合物的制备方法 | |
| CA2916805A1 (en) | N-(1-cyano-2-hydroxy-1-methyl-ethyl)-4-(trifluoromethylsulfanyl)benzamide derivatives for use as nematocidal drugs | |
| HK1178813A (en) | N-hydroxylsulfonamide derivatives as new physiologically useful nitroxyl donors |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM9A | Lapsed patents |
Effective date: 19960723 |