GB1583911A - Imidazopyridazines and their use as therapeutic agents - Google Patents
Imidazopyridazines and their use as therapeutic agents Download PDFInfo
- Publication number
- GB1583911A GB1583911A GB5289/77A GB528977A GB1583911A GB 1583911 A GB1583911 A GB 1583911A GB 5289/77 A GB5289/77 A GB 5289/77A GB 528977 A GB528977 A GB 528977A GB 1583911 A GB1583911 A GB 1583911A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- compound
- compounds
- hydrogen
- alkyl
- 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.)
- Expired
Links
- 239000003814 drug Substances 0.000 title description 2
- 150000005233 imidazopyridazines Chemical class 0.000 title description 2
- 229940124597 therapeutic agent Drugs 0.000 title description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 136
- 150000001875 compounds Chemical class 0.000 claims description 95
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 43
- -1 amine hydrochloride Chemical class 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 35
- 239000000243 solution Substances 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 26
- 239000004480 active ingredient Substances 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 238000010992 reflux Methods 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 claims description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
- 231100000252 nontoxic Toxicity 0.000 claims description 9
- 230000003000 nontoxic effect Effects 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 239000000706 filtrate Substances 0.000 claims description 7
- 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 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000002347 injection Methods 0.000 claims description 5
- 239000007924 injection Substances 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 239000012044 organic layer Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 150000004892 pyridazines Chemical class 0.000 claims description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- 239000000443 aerosol Substances 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 229960004977 anhydrous lactose Drugs 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002775 capsule Substances 0.000 claims description 4
- 239000007903 gelatin capsule Substances 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 4
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 4
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 4
- 229940016286 microcrystalline cellulose Drugs 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
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 239000006188 syrup Substances 0.000 claims description 4
- 235000020357 syrup Nutrition 0.000 claims description 4
- 239000008215 water for injection Substances 0.000 claims description 4
- 208000009079 Bronchial Spasm Diseases 0.000 claims description 3
- 208000014181 Bronchial disease Diseases 0.000 claims description 3
- 206010006482 Bronchospasm Diseases 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 238000006073 displacement reaction Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 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 description 3
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- RILNCPBFGQUIFR-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)NC(C(C)C)C1=NNC(C=C1)=O.Cl Chemical compound C(C1=CC=CC=C1)(=O)NC(C(C)C)C1=NNC(C=C1)=O.Cl RILNCPBFGQUIFR-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 229930006000 Sucrose Natural products 0.000 claims description 2
- 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 claims description 2
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 2
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 239000000796 flavoring agent Substances 0.000 claims description 2
- 235000019634 flavors Nutrition 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 2
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 2
- 229960001375 lactose Drugs 0.000 claims description 2
- 239000008101 lactose Substances 0.000 claims description 2
- 235000019359 magnesium stearate Nutrition 0.000 claims description 2
- 229920000609 methyl cellulose Polymers 0.000 claims description 2
- 239000001923 methylcellulose Substances 0.000 claims description 2
- 235000010981 methylcellulose Nutrition 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 150000002900 organolithium compounds Chemical class 0.000 claims description 2
- ZOCLAPYLSUCOGI-UHFFFAOYSA-M potassium hydrosulfide Chemical compound [SH-].[K+] ZOCLAPYLSUCOGI-UHFFFAOYSA-M 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- 230000002335 preservative effect Effects 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
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- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 238000010561 standard procedure Methods 0.000 claims description 2
- 239000005720 sucrose Substances 0.000 claims description 2
- 238000009495 sugar coating Methods 0.000 claims description 2
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- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 239000000047 product Substances 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
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- 239000003480 eluent Substances 0.000 description 1
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- IXZFDJXHLQQSGQ-UHFFFAOYSA-N ethyl 4-chloro-4-oxobutanoate Chemical compound CCOC(=O)CCC(Cl)=O IXZFDJXHLQQSGQ-UHFFFAOYSA-N 0.000 description 1
- KSDDQTRMPYGTHF-UHFFFAOYSA-N ethyl 5-(3-methylbutanoylamino)-4-oxohexanoate Chemical compound C(CC(C)C)(=O)NC(C(CCC(=O)OCC)=O)C KSDDQTRMPYGTHF-UHFFFAOYSA-N 0.000 description 1
- XOCVXDMTNJCTSJ-UHFFFAOYSA-N ethyl 5-(butanoylamino)-4-oxohexanoate Chemical compound C(CCC)(=O)NC(C(CCC(=O)OCC)=O)C XOCVXDMTNJCTSJ-UHFFFAOYSA-N 0.000 description 1
- ZBDAZLWLWDJXRM-UHFFFAOYSA-N ethyl 5-benzamido-4-oxohexanoate Chemical compound C(C1=CC=CC=C1)(=O)NC(C(CCC(=O)OCC)=O)C ZBDAZLWLWDJXRM-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
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- 150000007857 hydrazones Chemical class 0.000 description 1
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- 230000007246 mechanism Effects 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229960002052 salbutamol Drugs 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007944 soluble tablet Substances 0.000 description 1
- 239000003506 spasmogen Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/04—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having less than three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
- C07D237/14—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5289/77A GB1583911A (en) | 1977-02-09 | 1977-02-09 | Imidazopyridazines and their use as therapeutic agents |
| IE186/78A IE46317B1 (en) | 1977-02-09 | 1978-01-27 | Imidazopyridazines and their use as therapeutic agents |
| ZA00780554A ZA78554B (en) | 1977-02-09 | 1978-01-30 | Novel therapeutic agents |
| DK46078A DK46078A (da) | 1977-02-09 | 1978-01-31 | Fremgangsmaade til fremstilling af pyridazinderivater |
| NZ186370A NZ186370A (en) | 1977-02-09 | 1978-02-01 | 1-hydrocarbylimidazo (1,5-b)pyridazin-6(5h)-ones |
| FI780350A FI780350A (fi) | 1977-02-09 | 1978-02-03 | Nya terapeutiska medel |
| DE19782804909 DE2804909A1 (de) | 1977-02-09 | 1978-02-06 | Imidazo eckige klammer auf 1,5-b eckige klammer zu -pyridazine |
| NL7801469A NL7801469A (nl) | 1977-02-09 | 1978-02-08 | Nieuwe imidazo (1,5-b)-pyradizinen met farma- ceutische activiteit. |
| SE7801489A SE7801489L (sv) | 1977-02-09 | 1978-02-08 | Forfarande for framstellning av imidazo (1,5-b) pyridaziner |
| IT7847968A IT1155821B (it) | 1977-02-09 | 1978-02-08 | Imidazopiridazine sostituite e relativo procedimento di produzione |
| ES466795A ES466795A1 (es) | 1977-02-09 | 1978-02-08 | Un procedimiento para la produccion de imidazo(1,5-b)pirida-zinas |
| AU33122/78A AU515804B2 (en) | 1977-02-09 | 1978-02-08 | IMIDAZO (1, 5-b PYRIDAZINES |
| BE184997A BE863759A (fr) | 1977-02-09 | 1978-02-08 | Nouvelles imidazo (1,5-b) pyridazines et procede pour leur preparation |
| JP1403578A JPS53101397A (en) | 1977-02-09 | 1978-02-09 | Novel imidazo*1*55b*pyridazine process for preparing same medical composition containing same and therapeutic method using same |
| FR7803669A FR2380281A1 (fr) | 1977-02-09 | 1978-02-09 | Nouvelles imidazo(1,5-b)-pyridazines utiles comme medicaments |
| ES475120A ES475120A1 (es) | 1977-02-09 | 1978-11-15 | Un procedimiento para la preparacion de imidazo (1,5-b)piri-dazinas. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5289/77A GB1583911A (en) | 1977-02-09 | 1977-02-09 | Imidazopyridazines and their use as therapeutic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1583911A true GB1583911A (en) | 1981-02-04 |
Family
ID=9793329
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5289/77A Expired GB1583911A (en) | 1977-02-09 | 1977-02-09 | Imidazopyridazines and their use as therapeutic agents |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS53101397A (fr) |
| AU (1) | AU515804B2 (fr) |
| BE (1) | BE863759A (fr) |
| DE (1) | DE2804909A1 (fr) |
| DK (1) | DK46078A (fr) |
| ES (2) | ES466795A1 (fr) |
| FI (1) | FI780350A (fr) |
| FR (1) | FR2380281A1 (fr) |
| GB (1) | GB1583911A (fr) |
| IE (1) | IE46317B1 (fr) |
| IT (1) | IT1155821B (fr) |
| NL (1) | NL7801469A (fr) |
| NZ (1) | NZ186370A (fr) |
| SE (1) | SE7801489L (fr) |
| ZA (1) | ZA78554B (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0099080A2 (fr) * | 1982-07-12 | 1984-01-25 | The Dow Chemical Company | Tétrahydrotétrazolo(5,1-a)phthalazines substituées |
| EP0099081A2 (fr) * | 1982-07-12 | 1984-01-25 | The Dow Chemical Company | Tétrahydroimidazo(2,1-a)phthalazines substituées en 6 |
| EP0100461A2 (fr) * | 1982-07-12 | 1984-02-15 | The Dow Chemical Company | Tétrahydropyridazino(1,6-a)benzimidazoles substituées |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2473522A1 (fr) * | 1980-01-16 | 1981-07-17 | Synthelabo | Nouveaux derives substitues de dihydro-2,3 imidazo(1,2-b)pyridazines et les medicaments, utiles notamment comme antidepresseurs, qui en contiennent |
| GB8429694D0 (en) * | 1984-11-23 | 1985-01-03 | Glaxo Group Ltd | Chemical compounds |
| JPH07107404B2 (ja) * | 1991-04-22 | 1995-11-15 | 上西鉄工株式会社 | シリンダ装置 |
-
1977
- 1977-02-09 GB GB5289/77A patent/GB1583911A/en not_active Expired
-
1978
- 1978-01-27 IE IE186/78A patent/IE46317B1/en unknown
- 1978-01-30 ZA ZA00780554A patent/ZA78554B/xx unknown
- 1978-01-31 DK DK46078A patent/DK46078A/da not_active Application Discontinuation
- 1978-02-01 NZ NZ186370A patent/NZ186370A/xx unknown
- 1978-02-03 FI FI780350A patent/FI780350A/fi not_active Application Discontinuation
- 1978-02-06 DE DE19782804909 patent/DE2804909A1/de not_active Withdrawn
- 1978-02-08 ES ES466795A patent/ES466795A1/es not_active Expired
- 1978-02-08 AU AU33122/78A patent/AU515804B2/en not_active Expired
- 1978-02-08 BE BE184997A patent/BE863759A/fr unknown
- 1978-02-08 NL NL7801469A patent/NL7801469A/xx not_active Application Discontinuation
- 1978-02-08 SE SE7801489A patent/SE7801489L/xx unknown
- 1978-02-08 IT IT7847968A patent/IT1155821B/it active
- 1978-02-09 FR FR7803669A patent/FR2380281A1/fr active Granted
- 1978-02-09 JP JP1403578A patent/JPS53101397A/ja active Pending
- 1978-11-15 ES ES475120A patent/ES475120A1/es not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0099080A2 (fr) * | 1982-07-12 | 1984-01-25 | The Dow Chemical Company | Tétrahydrotétrazolo(5,1-a)phthalazines substituées |
| EP0099081A2 (fr) * | 1982-07-12 | 1984-01-25 | The Dow Chemical Company | Tétrahydroimidazo(2,1-a)phthalazines substituées en 6 |
| EP0100461A2 (fr) * | 1982-07-12 | 1984-02-15 | The Dow Chemical Company | Tétrahydropyridazino(1,6-a)benzimidazoles substituées |
| EP0100461A3 (en) * | 1982-07-12 | 1984-08-22 | The Dow Chemical Company | Substituted tetrahydropyridazino(1,6-a)benzimidazoles |
| EP0099081A3 (en) * | 1982-07-12 | 1984-08-29 | The Dow Chemical Company | 6-substituted tetrahydroimidazo(2,1-a)-phthalazines |
| EP0099080A3 (en) * | 1982-07-12 | 1984-08-29 | The Dow Chemical Company | Substituted tetrahydrotetrazolo(5,1-a)phthalazines |
Also Published As
| Publication number | Publication date |
|---|---|
| FI780350A (fi) | 1978-08-10 |
| DE2804909A1 (de) | 1978-08-10 |
| IT1155821B (it) | 1987-01-28 |
| NL7801469A (nl) | 1978-08-11 |
| SE7801489L (sv) | 1978-08-10 |
| ES475120A1 (es) | 1979-05-16 |
| ZA78554B (en) | 1978-12-27 |
| IE46317B1 (en) | 1983-05-04 |
| DK46078A (da) | 1978-08-10 |
| BE863759A (fr) | 1978-08-08 |
| AU515804B2 (en) | 1981-04-30 |
| IT7847968A0 (it) | 1978-02-08 |
| JPS53101397A (en) | 1978-09-04 |
| FR2380281A1 (fr) | 1978-09-08 |
| IE780186L (en) | 1978-08-19 |
| NZ186370A (en) | 1981-03-16 |
| FR2380281B1 (fr) | 1982-03-12 |
| AU3312278A (en) | 1979-08-16 |
| ES466795A1 (es) | 1979-01-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |