SK20199A3 - Ether muscarinic antagonists - Google Patents

Ether muscarinic antagonists Download PDF

Info

Publication number: SK20199A3
Authority: SK; Slovakia
Prior art keywords: alkyl; independently selected; cycloalkyl; group; substituted
Prior art date: 1996-08-15

Application number

SK201-99A

Other languages

English (en)

Slovak (sk)

Inventor

Yuguang Wang

Wei K Chang

Sundeep Dugar

Samuel Chackalamannil

Original Assignee

Schering Corp

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.)

1996-08-15

Filing date

1997-08-13

Publication date

2000-03-13

1997-08-13 Application filed by Schering Corp filed Critical Schering Corp

2000-03-13 Publication of SK20199A3 publication Critical patent/SK20199A3/sk

Links

229940121948 Muscarinic receptor antagonist Drugs 0.000 title abstract description 6
239000003149 muscarinic antagonist Substances 0.000 title abstract description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 7
150000001875 compounds Chemical class 0.000 claims abstract description 82
238000000034 method Methods 0.000 claims abstract description 26
125000000217 alkyl group Chemical group 0.000 claims abstract description 20
-1 1,4 Di-substituted piperidine Chemical class 0.000 claims abstract description 16
208000010877 cognitive disease Diseases 0.000 claims abstract description 15
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 15
150000003839 salts Chemical class 0.000 claims abstract description 12
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
238000002360 preparation method Methods 0.000 claims abstract description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
150000002148 esters Chemical class 0.000 claims abstract description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 98
125000003118 aryl group Chemical group 0.000 claims description 19
125000001072 heteroaryl group Chemical group 0.000 claims description 19
229910052799 carbon Inorganic materials 0.000 claims description 18
229910052736 halogen Inorganic materials 0.000 claims description 12
229940100578 Acetylcholinesterase inhibitor Drugs 0.000 claims description 9
239000000544 cholinesterase inhibitor Substances 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
208000015122 neurodegenerative disease Diseases 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
230000001149 cognitive effect Effects 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
230000004770 neurodegeneration Effects 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 5
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
125000004104 aryloxy group Chemical group 0.000 claims description 3
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims description 2
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 2
125000002757 morpholinyl group Chemical group 0.000 claims description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
208000024827 Alzheimer disease Diseases 0.000 abstract description 6
239000003112 inhibitor Substances 0.000 abstract description 4
239000012453 solvate Substances 0.000 abstract description 4
125000000392 cycloalkenyl group Chemical group 0.000 abstract description 2
125000003386 piperidinyl group Chemical group 0.000 abstract description 2
125000004076 pyridyl group Chemical group 0.000 abstract description 2
125000005346 substituted cycloalkyl group Chemical group 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 18
229960004373 acetylcholine Drugs 0.000 description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000000460 chlorine Substances 0.000 description 15
239000000203 mixture Substances 0.000 description 13
239000000243 solution Substances 0.000 description 13
102000005962 receptors Human genes 0.000 description 11
108020003175 receptors Proteins 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
230000027455 binding Effects 0.000 description 8
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FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 7
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 7
239000000523 sample Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
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125000004432 carbon atom Chemical group C* 0.000 description 6
239000007788 liquid 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
239000002904 solvent Substances 0.000 description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
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AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
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239000002552 dosage form Substances 0.000 description 4
239000012458 free base Substances 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
239000012528 membrane Substances 0.000 description 4
230000003551 muscarinic effect Effects 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
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OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 3
229960001231 choline Drugs 0.000 description 3
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229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000002287 radioligand Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 3
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
239000003643 water by type Substances 0.000 description 3
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
VSMDINRNYYEDRN-UHFFFAOYSA-N 4-iodophenol Chemical compound OC1=CC=C(I)C=C1 VSMDINRNYYEDRN-UHFFFAOYSA-N 0.000 description 2
VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical class O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
102000017926 CHRM2 Human genes 0.000 description 2
229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
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241001465754 Metazoa Species 0.000 description 2
102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 2
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NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
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125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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238000001727 in vivo Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000003780 insertion Methods 0.000 description 1
230000037431 insertion Effects 0.000 description 1
230000010354 integration Effects 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000010410 layer Substances 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical class C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
238000000520 microinjection Methods 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
239000007922 nasal spray Substances 0.000 description 1
229960001499 neostigmine bromide Drugs 0.000 description 1
LULNWZDBKTWDGK-UHFFFAOYSA-M neostigmine bromide Chemical compound [Br-].CN(C)C(=O)OC1=CC=CC([N+](C)(C)C)=C1 LULNWZDBKTWDGK-UHFFFAOYSA-M 0.000 description 1
210000001577 neostriatum Anatomy 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
230000009871 nonspecific binding Effects 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
125000005485 noradamantyl group Chemical group 0.000 description 1
125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000006201 parenteral dosage form Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000004926 polymethyl methacrylate Substances 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
230000003518 presynaptic effect Effects 0.000 description 1
238000012545 processing Methods 0.000 description 1
ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
238000011002 quantification Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
239000000565 sealant Substances 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 1
238000012956 testing procedure Methods 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
239000010936 titanium Substances 0.000 description 1
GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
- 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
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/96—Sulfur atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Neurosurgery (AREA)
Engineering & Computer Science (AREA)
Epidemiology (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SK201-99A 1996-08-15 1997-08-13 Ether muscarinic antagonists SK20199A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US70072296A	1996-08-15	1996-08-15
PCT/US1997/013894 WO1998006697A1 (en)	1996-08-15	1997-08-13	Ether muscarinic antagonists

Publications (1)

Publication Number	Publication Date
SK20199A3 true SK20199A3 (en)	2000-03-13

Family

ID=24814614

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK201-99A SK20199A3 (en)	1996-08-15	1997-08-13	Ether muscarinic antagonists

Country Status (19)

Country	Link
EP (1)	EP0922029B1 (cs)
JP (1)	JP3390179B2 (cs)
KR (1)	KR20000029976A (cs)
CN (1)	CN1155574C (cs)
AT (1)	ATE297381T1 (cs)
AU (1)	AU732096B2 (cs)
BR (1)	BR9711061A (cs)
CA (1)	CA2263167C (cs)
CZ (1)	CZ43399A3 (cs)
DE (1)	DE69733478T2 (cs)
ES (1)	ES2241053T3 (cs)
HU (1)	HUP9904363A3 (cs)
IL (1)	IL128524A0 (cs)
NO (1)	NO990671L (cs)
NZ (1)	NZ334017A (cs)
PL (1)	PL331536A1 (cs)
SK (1)	SK20199A3 (cs)
TR (1)	TR199900314T2 (cs)
WO (1)	WO1998006697A1 (cs)

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AU762726B2 (en) *	1998-03-31	2003-07-03	Acadia Pharmaceuticals, Inc.	Compounds with activity on muscarinic receptors
US6528529B1 (en)	1998-03-31	2003-03-04	Acadia Pharmaceuticals Inc.	Compounds with activity on muscarinic receptors
AU779354B2 (en)	1998-12-23	2005-01-20	Orphan Medical, Inc.	Microbiologically sound and stable solutions of gamma-hydroxybutyrate salt for the treatment of narcolepsy
US6387930B1 (en)	1999-05-04	2002-05-14	Schering Corporation	Piperidine derivatives useful as CCR5 antagonists
CZ301161B6 (cs) *	1999-05-04	2009-11-18	Schering Corporation	Piperidinopiperidylový derivát užitecný jako CCR5 antagonista, farmaceutický prostredek jej obsahující
US6635646B1 (en)	1999-05-04	2003-10-21	Schering Corporation	Pegylated interferon alfa-CCR5 antagonist combination HIV therapy
AR033517A1 (es)	2000-04-08	2003-12-26	Astrazeneca Ab	Derivados de piperidina, proceso para su preparacion y uso de estos derivados en la fabricacion de medicamentos
US7718650B2 (en)	2001-05-11	2010-05-18	Biovitrum Ab	Aryl sulfonamide compounds for treating obesity
CN1329382C (zh)	2001-05-11	2007-08-01	比奥维特罗姆股份公司	治疗肥胖、ⅱ型糖尿病和cns－疾病的芳基磺酰胺化合物
EP1604982A1 (en)	2001-07-02	2005-12-14	AstraZeneca AB	Intermediates for the preparation of piperidine derivatives useful as modulators of chemokine receptor activity
GB0120461D0 (en)	2001-08-22	2001-10-17	Astrazeneca Ab	Novel compounds
GB0122503D0 (en)	2001-09-18	2001-11-07	Astrazeneca Ab	Chemical compounds
KR100579813B1 (ko) *	2001-10-16	2006-05-12	주식회사 에스티씨나라	피페리딘 유도체, 이의 제조방법 및 이를 포함하는 치매치료용 약학적 조성물
DE10201550A1 (de) *	2002-01-17	2003-07-31	Merck Patent Gmbh	Phenoxy-Piperidine
SE0200843D0 (sv)	2002-03-19	2002-03-19	Astrazeneca Ab	Chemical compounds
SE0200844D0 (sv)	2002-03-19	2002-03-19	Astrazeneca Ab	Chemical compounds
WO2003105830A1 (ja) *	2002-06-14	2003-12-24	富山化学工業株式会社	脳機能を改善する医薬組成物および脳機能を改善するための方法
SE0202838D0 (sv) *	2002-09-24	2002-09-24	Astrazeneca Ab	Chemical compounds
SE0300957D0 (sv)	2003-04-01	2003-04-01	Astrazeneca Ab	Chemical compounds
SE0302956D0 (sv) *	2003-11-07	2003-11-07	Astrazeneca Ab	Chemical compounds
CA2581623A1 (en)	2004-09-23	2006-03-30	Reddy Us Therapeutics, Inc.	Novel pyridine compounds, process for their preparation and compositions containing them
TW200722419A (en) *	2005-05-27	2007-06-16	Astrazeneca Ab	Chemical compounds
WO2006126948A1 (en) *	2005-05-27	2006-11-30	Astrazeneca Ab	Piperidines for the treatment of chemokine mediated diseases
BRPI0613563A2 (pt)	2005-07-21	2012-01-17	Astrazeneca Ab	novos derivados de piperidina
DE102008008838A1 (de)	2008-02-13	2009-08-20	Bayer Healthcare Ag	Cycloalkoxy-substituierte 4-Phenyl-3,5-dicyanopyridine und ihre Verwendung
US9452980B2 (en)	2009-12-22	2016-09-27	Hoffmann-La Roche Inc.	Substituted benzamides
AU2011216950A1 (en)	2010-02-16	2012-08-23	Pfizer Inc.	(R)-4-((4-((4-(tetrahydrofuran-3-yloxy) benzo[d]isoxazol-3-yloxy)methyl)piperidin-1-yl)methyl)tetrahydro-2H-pyran-4-ol, a partial agonist of 5-HT4 receptors
MY195528A (en)	2016-03-17	2023-01-30	Hoffmann La Roche	5-Ethyl-4-Methyl-Pyrazole-3-Carboxamide Derivative Having Activity as Agonist of Taar
WO2018112842A1 (en)	2016-12-22	2018-06-28	Merck Sharp & Dohme Corp.	6,6-fused heteroaryl piperidine ether allosteric modulators of m4 muscarinic acetylcholine receptor
WO2018112843A1 (en)	2016-12-22	2018-06-28	Merck Sharp & Dohme Corp.	Heteroaryl piperidine ether allosteric modulators of the m4 muscarinic acetylcholine receptor
WO2018112840A1 (en) *	2016-12-22	2018-06-28	Merck Sharp & Dohme Corp.	6, 5-fused heteroaryl piperidine ether allosteric modulators of the m4 muscarinic acetylcholine receptor

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NZ296210A (en)	1994-12-02	1998-05-27	Yamanouchi Pharma Co Ltd	Amidinonaphthyl derivatives to inhibit activated blood coagulation factor x
IL117149A0 (en) *	1995-02-23	1996-06-18	Schering Corp	Muscarinic antagonists
ATE256110T1 (de) *	1995-09-15	2003-12-15	Neurosearch As	Piperindinverbindungen als calcium-kanal-blocker

1997
- 1997-08-13 CZ CZ99433A patent/CZ43399A3/cs unknown
- 1997-08-13 KR KR1019997001227A patent/KR20000029976A/ko not_active Withdrawn
- 1997-08-13 JP JP50985498A patent/JP3390179B2/ja not_active Expired - Fee Related
- 1997-08-13 TR TR1999/00314T patent/TR199900314T2/xx unknown
- 1997-08-13 AU AU39732/97A patent/AU732096B2/en not_active Ceased
- 1997-08-13 SK SK201-99A patent/SK20199A3/sk unknown
- 1997-08-13 BR BR9711061A patent/BR9711061A/pt unknown
- 1997-08-13 ES ES97937152T patent/ES2241053T3/es not_active Expired - Lifetime
- 1997-08-13 HU HU9904363A patent/HUP9904363A3/hu unknown
- 1997-08-13 PL PL97331536A patent/PL331536A1/xx unknown
- 1997-08-13 DE DE69733478T patent/DE69733478T2/de not_active Expired - Fee Related
- 1997-08-13 NZ NZ334017A patent/NZ334017A/xx unknown
- 1997-08-13 IL IL12852497A patent/IL128524A0/xx unknown
- 1997-08-13 CN CNB971985588A patent/CN1155574C/zh not_active Expired - Fee Related
- 1997-08-13 AT AT97937152T patent/ATE297381T1/de not_active IP Right Cessation
- 1997-08-13 EP EP97937152A patent/EP0922029B1/en not_active Expired - Lifetime
- 1997-08-13 WO PCT/US1997/013894 patent/WO1998006697A1/en not_active Ceased
- 1997-08-13 CA CA002263167A patent/CA2263167C/en not_active Expired - Fee Related
1999
- 1999-02-12 NO NO990671A patent/NO990671L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
CN1155574C (zh)	2004-06-30
JP2000500786A (ja)	2000-01-25
CN1232453A (zh)	1999-10-20
ATE297381T1 (de)	2005-06-15
IL128524A0 (en)	2000-01-31
BR9711061A (pt)	1999-08-17
DE69733478D1 (de)	2005-07-14
NO990671D0 (no)	1999-02-12
NZ334017A (en)	2000-04-28
JP3390179B2 (ja)	2003-03-24
KR20000029976A (ko)	2000-05-25
NO990671L (no)	1999-04-15
ES2241053T3 (es)	2005-10-16
TR199900314T2 (xx)	1999-05-21
WO1998006697A1 (en)	1998-02-19
HUP9904363A2 (hu)	2000-11-28
EP0922029B1 (en)	2005-06-08
DE69733478T2 (de)	2005-11-03
CA2263167A1 (en)	1998-02-19
CA2263167C (en)	2006-02-14
EP0922029A1 (en)	1999-06-16
AU3973297A (en)	1998-03-06
HUP9904363A3 (en)	2000-12-28
PL331536A1 (en)	1999-07-19
AU732096B2 (en)	2001-04-12
CZ43399A3 (cs)	1999-07-14

Publication	Publication Date	Title
CA2263167C (en)	2006-02-14	Ether muscarinic antagonists
US6294554B1 (en)	2001-09-25	Muscarinic antagonists
EP0811002B1 (en)	2004-01-21	Benzylpiperidines and piperazines as muscarinic antagonists
US5977138A (en)	1999-11-02	Ether muscarinic antagonists
EP1675847B1 (en)	2012-12-05	Spirocyclic heterocyclic derivatives and methods of their use
AU728592B2 (en)	2001-01-11	1,4-di-sustituted piperidines as muscarinic antagonists
EP0912534B1 (en)	2002-09-25	Muscarinic antagonists
EP1870405A1 (en)	2007-12-26	Carbonylated (Aza)cyclohexanes as dopamine D3 receptor ligands
US5744483A (en)	1998-04-28	Neuroprotective compounds
EP1214299B1 (en)	2004-04-14	Muscarinic antagonists
EP1976842B1 (en)	2010-03-10	Modulators of alpha7 nicotinic acetylcholine receptors and therapeutic uses thereof
US8772319B2 (en)	2014-07-08	Diagnostic and therapeutic alkyl piperidine/piperazine compounds and process
EP1785415B1 (en)	2012-05-02	Piperidine derivative or pharmaceutically acceptable salt thereof
MXPA99001500A (en)	1999-06-01	Ether muscarinic antagonists
SK286483B6 (sk)	2008-11-06	Opticky aktívne inhibítory biosyntézy cholesterolu, spôsob ich prípravy a použitie