AP455A - 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 PDF

Info

Publication number: AP455A
Authority: AP; ARIPO
Prior art keywords: compounds; preparation; oxatriazole; alkyl; imine
Prior art date: 1992-08-10

Application number

APAP/P/1993/000559A

Other languages

English (en)

Other versions

AP9300559A0 (en

Inventor

Gunnar Leo Karup

Herbert Fritz Preikschat

Søren Bols Pedersen

Tim Niss Corell

Børge Ingvar Frisch Alhede

Original Assignee

A/S Gea Farm Fabrik

Priority date (The priority date 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 date listed.)

1992-08-10

Filing date

1993-07-26

Publication date

1996-01-19

1993-07-26 Application filed by A/S Gea Farm Fabrik filed Critical A/S Gea Farm Fabrik

1993-10-31 Publication of AP9300559A0 publication Critical patent/AP9300559A0/xx

1996-01-19 Application granted granted Critical

1996-01-19 Publication of AP455A publication Critical patent/AP455A/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 46
238000002360 preparation method Methods 0.000 title claims abstract description 21
239000003814 drug Substances 0.000 title claims abstract description 16
238000000034 method Methods 0.000 title claims abstract description 9
239000000825 pharmaceutical preparation Substances 0.000 title claims abstract description 6
QPTISOPQFLIZCY-UHFFFAOYSA-N oxatriazol-5-amine Chemical class NC1=NN=NO1 QPTISOPQFLIZCY-UHFFFAOYSA-N 0.000 title claims abstract description 5
208000006673 asthma Diseases 0.000 claims abstract description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 25
-1 nitro, cyano, phenyl Chemical group 0.000 claims description 16
125000003118 aryl group Chemical group 0.000 claims description 11
210000001772 blood platelet Anatomy 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 8
150000002466 imines Chemical class 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 5
208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
230000002401 inhibitory effect Effects 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
201000001881 impotence Diseases 0.000 claims description 3
201000011461 pre-eclampsia Diseases 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
230000004071 biological effect Effects 0.000 abstract description 6
208000007536 Thrombosis Diseases 0.000 abstract description 5
208000024172 Cardiovascular disease Diseases 0.000 abstract description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
239000000203 mixture Substances 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
229910052757 nitrogen Inorganic materials 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 17
239000000047 product Substances 0.000 description 17
238000001914 filtration Methods 0.000 description 15
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
230000008018 melting Effects 0.000 description 12
238000002844 melting Methods 0.000 description 12
229910052717 sulfur Inorganic materials 0.000 description 12
238000000921 elemental analysis Methods 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
229910002092 carbon dioxide Inorganic materials 0.000 description 9
238000011161 development Methods 0.000 description 9
210000000056 organ Anatomy 0.000 description 9
239000000126 substance Substances 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
239000001569 carbon dioxide Substances 0.000 description 8
230000000694 effects Effects 0.000 description 8
238000012360 testing method Methods 0.000 description 8
230000002776 aggregation Effects 0.000 description 7
238000004220 aggregation Methods 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
238000003756 stirring Methods 0.000 description 7
230000005764 inhibitory process Effects 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
210000003437 trachea Anatomy 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
230000005540 biological transmission Effects 0.000 description 5
230000008602 contraction Effects 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
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 4
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 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
125000005233 alkylalcohol group Chemical group 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
239000008280 blood Substances 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000013558 reference substance Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
VPJXQGSRWJZDOB-UHFFFAOYSA-O 2-carbamoyloxyethyl(trimethyl)azanium Chemical compound C[N+](C)(C)CCOC(N)=O VPJXQGSRWJZDOB-UHFFFAOYSA-O 0.000 description 2
239000005864 Sulphur Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000000872 buffer Substances 0.000 description 2
238000005119 centrifugation 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
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 2
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
229960003711 glyceryl trinitrate Drugs 0.000 description 2
238000012417 linear regression Methods 0.000 description 2
239000012071 phase Substances 0.000 description 2
210000002381 plasma Anatomy 0.000 description 2
230000000328 pro-aggregatory effect Effects 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000002040 relaxant effect Effects 0.000 description 2
230000000241 respiratory effect Effects 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
229940083618 sodium nitroprusside Drugs 0.000 description 2
239000007858 starting material Substances 0.000 description 2
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
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
241000700199 Cavia porcellus Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
241000282619 Hylobates lar Species 0.000 description 1
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 1
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
230000004931 aggregating effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
HGARASNDAGOAPG-UHFFFAOYSA-N anisole;sulfuryl diisocyanate Chemical compound COC1=CC=CC=C1.O=C=NS(=O)(=O)N=C=O HGARASNDAGOAPG-UHFFFAOYSA-N 0.000 description 1
125000004429 atom Chemical group 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
238000006243 chemical reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
230000010339 dilation Effects 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
238000011067 equilibration Methods 0.000 description 1
LHLIGPDDSKJRQN-UHFFFAOYSA-N ethyl 2-isocyanato-3-phenylpropanoate Chemical compound CCOC(=O)C(N=C=O)CC1=CC=CC=C1 LHLIGPDDSKJRQN-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
CFEPCPHKICBCJV-UHFFFAOYSA-N ethyl 4-isocyanatobenzoate Chemical compound CCOC(=O)C1=CC=C(N=C=O)C=C1 CFEPCPHKICBCJV-UHFFFAOYSA-N 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
238000003760 magnetic stirring Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
XLFWDASMENKTKL-UHFFFAOYSA-N molsidomine Chemical class O1C(N=C([O-])OCC)=C[N+](N2CCOCC2)=N1 XLFWDASMENKTKL-UHFFFAOYSA-N 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
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
CQDAMYNQINDRQC-UHFFFAOYSA-N oxatriazole Chemical group C1=NN=NO1 CQDAMYNQINDRQC-UHFFFAOYSA-N 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
238000000746 purification Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 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
238000006467 substitution reaction Methods 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 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

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)

APAP/P/1993/000559A 1992-08-10 1993-07-26 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. AP455A (en)

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
AP9300559A0 AP9300559A0 (en)	1993-10-31
AP455A true AP455A (en)	1996-01-19

Family

ID=8099920

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
APAP/P/1993/000559A AP455A (en)	1992-08-10	1993-07-26	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 (is)
JP (1)	JPH07509703A (is)
CN (1)	CN1086813A (is)
AP (1)	AP455A (is)
AT (1)	ATE136893T1 (is)
AU (1)	AU4418193A (is)
BG (1)	BG99378A (is)
BR (1)	BR9306880A (is)
CA (1)	CA2140641A1 (is)
CZ (1)	CZ33995A3 (is)
DE (1)	DE69302279T2 (is)
DK (2)	DK100392D0 (is)
EE (1)	EE9400084A (is)
ES (1)	ES2085787T3 (is)
FI (1)	FI950575A0 (is)
GR (1)	GR3019681T3 (is)
HU (1)	HUT71230A (is)
IS (1)	IS4052A (is)
LT (1)	LT3054B (is)
LV (1)	LV10263B (is)
MX (1)	MX9304788A (is)
NZ (1)	NZ253681A (is)
OA (1)	OA10127A (is)
PL (1)	PL307395A1 (is)
RU (1)	RU95106464A (is)
SI (1)	SI9300425A (is)
SK (1)	SK18295A3 (is)
WO (1)	WO1994003442A1 (is)
ZA (1)	ZA935199B (is)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
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

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2015878B (en)	1978-03-10	1982-05-26	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 WO PCT/DK1993/000234 patent/WO1994003442A1/en not_active Ceased
- 1993-07-08 CZ CZ95339A patent/CZ33995A3/cs unknown
- 1993-07-08 RU RU95106464/04A patent/RU95106464A/ru unknown
- 1993-07-08 JP JP6504904A patent/JPH07509703A/ja active Pending
- 1993-07-08 DE DE69302279T patent/DE69302279T2/de not_active Expired - Fee Related
- 1993-07-08 HU HU9500401A patent/HUT71230A/hu unknown
- 1993-07-08 NZ NZ253681A patent/NZ253681A/en unknown
- 1993-07-08 SK SK182-95A patent/SK18295A3/sk unknown
- 1993-07-08 PL PL93307395A patent/PL307395A1/xx unknown
- 1993-07-08 CA CA002140641A patent/CA2140641A1/en not_active Abandoned
- 1993-07-08 BR BR9306880A patent/BR9306880A/pt not_active Application Discontinuation
- 1993-07-08 DK DK93914656.9T patent/DK0654028T3/da active
- 1993-07-08 AU AU44181/93A patent/AU4418193A/en not_active Abandoned
- 1993-07-08 ES ES93914656T patent/ES2085787T3/es not_active Expired - Lifetime
- 1993-07-08 EP EP93914656A patent/EP0654028B1/en not_active Expired - Lifetime
- 1993-07-08 AT AT93914656T patent/ATE136893T1/de active
- 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 CN CN93109277A patent/CN1086813A/zh active Pending
- 1993-08-10 SI SI9300425A patent/SI9300425A/sl unknown
- 1993-08-10 LV LVP-93-1027A patent/LV10263B/en unknown
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/FI950575A0/fi not_active Application Discontinuation
- 1995-02-10 OA OA60609A patent/OA10127A/en unknown
1996
- 1996-04-19 GR GR960401060T patent/GR3019681T3/el unknown

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* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Volume 73, No. 17, 26 October 1970, (Columbus, Ohio, US), see page 361, Abstract 87922f; & JP,B,45 021 102 (17 July 1970) *
CHEMICAL ABSTRACTS, Volume 73, No. 17, 26 October 1970, (Columbus, Ohio, US), see page 362, Abstract 87930g; & JP,B,45 020 904 (Mesoionic Compounds) 15 July 1970 *

Also Published As

Publication number	Publication date
ES2085787T3 (es)	1996-06-01
SK18295A3 (en)	1995-07-11
ATE136893T1 (de)	1996-05-15
DK0654028T3 (da)	1996-07-29
LT3054B (en)	1994-10-25
EP0654028A1 (en)	1995-05-24
AP9300559A0 (en)	1993-10-31
FI950575A7 (fi)	1995-02-09
MX9304788A (es)	1994-02-28
CZ33995A3 (en)	1995-09-13
IS4052A (is)	1994-02-11
BR9306880A (pt)	1998-12-08
WO1994003442A1 (en)	1994-02-17
DE69302279D1 (de)	1996-05-23
GR3019681T3 (en)	1996-07-31
LV10263A (lv)	1994-10-20
DE69302279T2 (de)	1996-09-19
RU95106464A (ru)	1996-12-27
FI950575A0 (fi)	1995-02-09
EE9400084A (et)	1995-12-15
AU4418193A (en)	1994-03-03
NZ253681A (en)	1995-09-26
DK100392D0 (da)	1992-08-10
EP0654028B1 (en)	1996-04-17
OA10127A (en)	1996-12-18
JPH07509703A (ja)	1995-10-26
ZA935199B (en)	1994-03-02
BG99378A (bg)	1995-11-30
CN1086813A (zh)	1994-05-18
LTIP816A (en)	1994-05-15
PL307395A1 (en)	1995-05-15
LV10263B (en)	1995-06-20
SI9300425A (en)	1994-03-31
HU9500401D0 (en)	1995-03-28
CA2140641A1 (en)	1994-02-17
HUT71230A (en)	1995-11-28

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