OA10838A - Oxa-and thia-diazole muscarinic receptor antagonists - Google Patents
Oxa-and thia-diazole muscarinic receptor antagonists Download PDFInfo
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- OA10838A OA10838A OA9800143A OA9800143A OA10838A OA 10838 A OA10838 A OA 10838A OA 9800143 A OA9800143 A OA 9800143A OA 9800143 A OA9800143 A OA 9800143A OA 10838 A OA10838 A OA 10838A
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- compound
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- alkyl
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- 229940121948 Muscarinic receptor antagonist Drugs 0.000 title abstract description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 title description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- -1 aryl-(C1-C4 alkyl) Chemical group 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 206010046543 Urinary incontinence Diseases 0.000 claims abstract description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 4
- 208000002551 irritable bowel syndrome Diseases 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical group [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 208000026139 Memory disease Diseases 0.000 claims description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 208000012258 Diverticular disease Diseases 0.000 claims description 2
- 206010013554 Diverticulum Diseases 0.000 claims description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 2
- 125000004188 dichlorophenyl group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 2
- 125000005905 mesyloxy group Chemical group 0.000 claims description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 2
- SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 9
- 125000001475 halogen functional group Chemical group 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 3
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 229940124024 weight reducing agent Drugs 0.000 claims 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 238000004128 high performance liquid chromatography Methods 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 229960001407 sodium bicarbonate Drugs 0.000 claims 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 6
- 230000019771 cognition Effects 0.000 abstract description 2
- 239000003623 enhancer Substances 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 229940093499 ethyl acetate Drugs 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 238000010992 reflux Methods 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 11
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- 239000008367 deionised water Substances 0.000 description 10
- 238000003818 flash chromatography Methods 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 210000003932 urinary bladder Anatomy 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 150000004795 grignard reagents Chemical class 0.000 description 4
- 210000003405 ileum Anatomy 0.000 description 4
- NNICRUQPODTGRU-UHFFFAOYSA-N mandelonitrile Chemical compound N#CC(O)C1=CC=CC=C1 NNICRUQPODTGRU-UHFFFAOYSA-N 0.000 description 4
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- 229910021653 sulphate ion Inorganic materials 0.000 description 4
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000556 agonist Substances 0.000 description 3
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical group [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 208000027771 Obstructive airways disease Diseases 0.000 description 2
- 206010030136 Oesophageal achalasia Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- AQGCSYOSUOICDV-UHFFFAOYSA-N cyclobutyl-phenyl-(5-piperidin-4-yl-1,2,4-oxadiazol-3-yl)methanol Chemical compound N=1OC(C2CCNCC2)=NC=1C(C=1C=CC=CC=1)(O)C1CCC1 AQGCSYOSUOICDV-UHFFFAOYSA-N 0.000 description 2
- 231100000673 dose–response relationship Toxicity 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 239000006260 foam Substances 0.000 description 2
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- 238000001990 intravenous administration Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000003551 muscarinic effect Effects 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
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- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
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- 230000005526 G1 to G0 transition Effects 0.000 description 1
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- 229910052744 lithium Inorganic materials 0.000 description 1
- SNHOZPMHMQQMNI-UHFFFAOYSA-N lithium;2h-thiophen-2-ide Chemical compound [Li+].C=1C=[C-]SC=1 SNHOZPMHMQQMNI-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 206010027175 memory impairment Diseases 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229940083608 sodium hydroxide Drugs 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 238000007514 turning Methods 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9603755.1A GB9603755D0 (en) | 1996-02-22 | 1996-02-22 | Therapeutic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA10838A true OA10838A (en) | 2001-08-13 |
Family
ID=10789217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA9800143A OA10838A (en) | 1996-02-22 | 1998-08-14 | Oxa-and thia-diazole muscarinic receptor antagonists |
Country Status (42)
| Country | Link |
|---|---|
| US (1) | US5977142A (cs) |
| EP (1) | EP0885218B1 (cs) |
| JP (1) | JP3148252B2 (cs) |
| KR (1) | KR100315934B1 (cs) |
| CN (1) | CN1089340C (cs) |
| AP (1) | AP751A (cs) |
| AR (1) | AR005916A1 (cs) |
| AT (1) | ATE200899T1 (cs) |
| AU (1) | AU712230B2 (cs) |
| BG (2) | BG102699A (cs) |
| BR (1) | BR9707733A (cs) |
| CA (1) | CA2247164C (cs) |
| CO (1) | CO4650040A1 (cs) |
| CZ (1) | CZ292650B6 (cs) |
| DE (1) | DE69704701T2 (cs) |
| DK (1) | DK0885218T3 (cs) |
| DZ (1) | DZ2181A1 (cs) |
| ES (1) | ES2156357T3 (cs) |
| GB (1) | GB9603755D0 (cs) |
| GR (1) | GR3036032T3 (cs) |
| HN (1) | HN1997000020A (cs) |
| HR (1) | HRP970098B1 (cs) |
| HU (1) | HUP9900501A3 (cs) |
| ID (1) | ID16642A (cs) |
| IL (1) | IL125413A (cs) |
| IS (1) | IS4803A (cs) |
| MY (1) | MY129729A (cs) |
| NO (1) | NO313414B1 (cs) |
| NZ (1) | NZ331039A (cs) |
| OA (1) | OA10838A (cs) |
| PE (1) | PE42798A1 (cs) |
| PL (1) | PL186879B1 (cs) |
| PT (1) | PT885218E (cs) |
| RU (1) | RU2162848C2 (cs) |
| SK (1) | SK283461B6 (cs) |
| TN (1) | TNSN97039A1 (cs) |
| TR (1) | TR199801644T2 (cs) |
| TW (1) | TW492961B (cs) |
| UA (1) | UA61068C2 (cs) |
| WO (1) | WO1997030994A1 (cs) |
| YU (1) | YU35698A (cs) |
| ZA (1) | ZA971513B (cs) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6107313A (en) * | 1998-10-02 | 2000-08-22 | Combichem, Inc. | Dopamine receptor antagonists |
| ATE375340T1 (de) * | 2001-02-21 | 2007-10-15 | Nps Pharma Inc | Heteropolycyclische verbindungen und deren verwendung als metabotrope glutamatrezeptorantagonisten |
| GB0510139D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B1 |
| GB0510141D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B3 |
| GB0516313D0 (en) * | 2005-08-08 | 2005-09-14 | Argenta Discovery Ltd | Azole derivatives and their uses |
| WO2008017827A2 (en) * | 2006-08-08 | 2008-02-14 | Argenta Discovery Limited | Azole and thiazole derivatives and their uses |
| JP2010501533A (ja) * | 2006-08-21 | 2010-01-21 | アージェンタ ディスカバリー リミテッド | Ｍ３レセプター調節物質として有用な窒素含有複素環化合物 |
| WO2008096093A1 (en) * | 2007-02-06 | 2008-08-14 | Argenta Discovery Ltd. | Oxazole and thiazole derivatives and their uses |
| GB0702416D0 (en) * | 2007-02-07 | 2007-03-21 | Argenta Discovery Ltd | New combination |
| GB0702385D0 (en) * | 2007-02-07 | 2007-03-21 | Argenta Discovery Ltd | New combination |
| BRPI0807004A2 (pt) * | 2007-02-07 | 2014-04-15 | Argenta Discovery Ltd | Sal |
| GB0702414D0 (en) * | 2007-02-07 | 2007-03-21 | Argenta Discovery Ltd | Oxazole and thiazole derivatives and their uses 2 |
| GB0702382D0 (en) * | 2007-02-07 | 2007-03-21 | Argenta Discovery Ltd | New salt |
| RU2009133258A (ru) * | 2007-02-15 | 2011-03-20 | Арджента Дискавери Лимитед (Gb) | Гетероциклические производные в качестве ингибиторов мускариновых рецепторов типа мз |
| WO2009098453A1 (en) * | 2008-02-06 | 2009-08-13 | Astrazeneca Ab | Azonia bicycloalkanes as m3 muscarinic acetylcholin receptor antagonists |
| US8263623B2 (en) | 2008-07-11 | 2012-09-11 | Pfizer Inc. | Triazol derivatives useful for the treatment of diseases |
| WO2010018352A1 (en) * | 2008-08-12 | 2010-02-18 | Argenta Discovery Limited | Heterocyclic compounds used in the treatment of diseases where enhanced m3 receptor activation is implicated |
| JP2014065387A (ja) * | 2012-09-25 | 2014-04-17 | Showa Corp | 自動二輪車の車高調整装置 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ219646A (en) * | 1986-03-27 | 1990-10-26 | Merck Sharp & Dohme | Oxadiazole derivatives of azacyclics for treating cns disorders |
| IL88846A0 (en) * | 1988-01-08 | 1989-07-31 | Merck Sharp & Dohme | Lipophilic oxadiazoles,their preparation and pharmaceutical compositions containing them |
| US5043345A (en) * | 1989-02-22 | 1991-08-27 | Novo Nordisk A/S | Piperidine compounds and their preparation and use |
| AU3171493A (en) * | 1991-12-31 | 1993-07-28 | Fujisawa Pharmaceutical Co., Ltd. | Oxadiazole derivatives having acetylcholinesterase-inhibitory and muscarinic agonist activity |
| TW360653B (en) * | 1995-03-01 | 1999-06-11 | Janssen Pharmaceutica Nv | A oxadiazole compound having colon motility stimulating properties, its preparation process and its pharmaceutical composition |
-
1996
- 1996-02-22 GB GBGB9603755.1A patent/GB9603755D0/en active Pending
-
1997
- 1997-01-21 TW TW086100642A patent/TW492961B/zh not_active IP Right Cessation
- 1997-02-03 HN HN1997000020A patent/HN1997000020A/es unknown
- 1997-02-04 WO PCT/EP1997/000525 patent/WO1997030994A1/en active IP Right Grant
- 1997-02-04 JP JP52974197A patent/JP3148252B2/ja not_active Expired - Fee Related
- 1997-02-04 BR BR9707733A patent/BR9707733A/pt not_active Application Discontinuation
- 1997-02-04 NZ NZ331039A patent/NZ331039A/en unknown
- 1997-02-04 TR TR1998/01644T patent/TR199801644T2/xx unknown
- 1997-02-04 EP EP97902337A patent/EP0885218B1/en not_active Expired - Lifetime
- 1997-02-04 HU HU9900501A patent/HUP9900501A3/hu unknown
- 1997-02-04 CZ CZ19982678A patent/CZ292650B6/cs not_active IP Right Cessation
- 1997-02-04 DK DK97902337T patent/DK0885218T3/da active
- 1997-02-04 PT PT97902337T patent/PT885218E/pt unknown
- 1997-02-04 PL PL97328633A patent/PL186879B1/pl not_active IP Right Cessation
- 1997-02-04 SK SK1123-98A patent/SK283461B6/sk unknown
- 1997-02-04 IL IL12541397A patent/IL125413A/en not_active IP Right Cessation
- 1997-02-04 CA CA002247164A patent/CA2247164C/en not_active Expired - Fee Related
- 1997-02-04 AT AT97902337T patent/ATE200899T1/de not_active IP Right Cessation
- 1997-02-04 US US09/117,556 patent/US5977142A/en not_active Expired - Fee Related
- 1997-02-04 KR KR1019980706534A patent/KR100315934B1/ko not_active Expired - Fee Related
- 1997-02-04 RU RU98117457/04A patent/RU2162848C2/ru not_active IP Right Cessation
- 1997-02-04 ES ES97902337T patent/ES2156357T3/es not_active Expired - Lifetime
- 1997-02-04 AU AU16014/97A patent/AU712230B2/en not_active Ceased
- 1997-02-04 DE DE69704701T patent/DE69704701T2/de not_active Expired - Fee Related
- 1997-02-04 CN CN97192486A patent/CN1089340C/zh not_active Expired - Fee Related
- 1997-02-13 CO CO97007550A patent/CO4650040A1/es unknown
- 1997-02-14 PE PE1997000104A patent/PE42798A1/es not_active Application Discontinuation
- 1997-02-19 TN TNTNSN97039A patent/TNSN97039A1/fr unknown
- 1997-02-19 DZ DZ970027A patent/DZ2181A1/fr active
- 1997-02-20 HR HR970098A patent/HRP970098B1/xx not_active IP Right Cessation
- 1997-02-20 AR ARP970100667A patent/AR005916A1/es unknown
- 1997-02-20 AP APAP/P/1997/000930A patent/AP751A/en active
- 1997-02-21 ID IDP970521A patent/ID16642A/id unknown
- 1997-02-21 MY MYPI97000654A patent/MY129729A/en unknown
- 1997-02-21 ZA ZA971513A patent/ZA971513B/xx unknown
- 1997-04-02 UA UA98094939A patent/UA61068C2/uk unknown
-
1998
- 1998-07-21 IS IS4803A patent/IS4803A/is unknown
- 1998-08-14 OA OA9800143A patent/OA10838A/en unknown
- 1998-08-19 BG BG102699A patent/BG102699A/xx unknown
- 1998-08-19 BG BG102699A patent/BG63971B1/bg unknown
- 1998-08-21 NO NO19983871A patent/NO313414B1/no not_active IP Right Cessation
- 1998-08-21 YU YU35698A patent/YU35698A/sh unknown
-
2001
- 2001-06-13 GR GR20010400885T patent/GR3036032T3/el not_active IP Right Cessation
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