KR20020063175A - 니코틴 수용체 작용물질의 양성 조절자 - Google Patents
니코틴 수용체 작용물질의 양성 조절자 Download PDFInfo
- Publication number
- KR20020063175A KR20020063175A KR1020027005705A KR20027005705A KR20020063175A KR 20020063175 A KR20020063175 A KR 20020063175A KR 1020027005705 A KR1020027005705 A KR 1020027005705A KR 20027005705 A KR20027005705 A KR 20027005705A KR 20020063175 A KR20020063175 A KR 20020063175A
- Authority
- KR
- South Korea
- Prior art keywords
- methyl
- indole
- disease
- hydroxy
- carboxamide
- 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.)
- Ceased
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- 239000000018 receptor agonist Substances 0.000 title claims description 43
- 229940044601 receptor agonist Drugs 0.000 title claims description 43
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 title description 2
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 136
- 229960002715 nicotine Drugs 0.000 claims abstract description 74
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims abstract description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 57
- 239000001257 hydrogen Substances 0.000 claims abstract description 57
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims abstract description 50
- 238000000034 method Methods 0.000 claims abstract description 49
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 38
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 36
- 201000010099 disease Diseases 0.000 claims abstract description 20
- 238000011282 treatment Methods 0.000 claims abstract description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 239000000556 agonist Substances 0.000 claims abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- 239000001301 oxygen Substances 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 10
- 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 abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims abstract description 7
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims abstract description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 239000011593 sulfur Substances 0.000 claims abstract description 7
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 4
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 208000035475 disorder Diseases 0.000 claims description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 14
- 230000006735 deficit Effects 0.000 claims description 13
- -1 (4-benzyl) oxazolin-2-yl Chemical group 0.000 claims description 12
- 208000024827 Alzheimer disease Diseases 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
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- 239000003814 drug Substances 0.000 claims description 5
- VIGGBSWKZAAVBB-AWEZNQCLSA-N 4-hydroxy-n-[(1r)-2-hydroxy-1-phenylethyl]-1-methylindole-2-carboxamide Chemical compound C1([C@H](CO)NC(=O)C=2N(C3=CC=CC(O)=C3C=2)C)=CC=CC=C1 VIGGBSWKZAAVBB-AWEZNQCLSA-N 0.000 claims description 3
- 206010068887 Tobacco poisoning Diseases 0.000 claims description 3
- 230000001149 cognitive effect Effects 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- NCFRPTLPGWKEIX-UHFFFAOYSA-N ethyl 4-hydroxy-1-methylindole-2-carboxylate Chemical compound C1=CC=C2N(C)C(C(=O)OCC)=CC2=C1O NCFRPTLPGWKEIX-UHFFFAOYSA-N 0.000 claims description 3
- YCZADCRYQVJCLW-UHFFFAOYSA-N (4-hydroxy-1-methylindol-2-yl)-pyrrolidin-1-ylmethanone Chemical compound C=1C2=C(O)C=CC=C2N(C)C=1C(=O)N1CCCC1 YCZADCRYQVJCLW-UHFFFAOYSA-N 0.000 claims description 2
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- HCMUPTQEYTYGHB-UHFFFAOYSA-N 4-hydroxy-1-methyl-n-(2-phenylethyl)indole-2-carboxamide Chemical compound C=1C2=C(O)C=CC=C2N(C)C=1C(=O)NCCC1=CC=CC=C1 HCMUPTQEYTYGHB-UHFFFAOYSA-N 0.000 claims description 2
- VNUZXARZRWELJO-UHFFFAOYSA-N 4-hydroxy-1-methyl-n-(4-phenylbutyl)indole-2-carboxamide Chemical compound C=1C2=C(O)C=CC=C2N(C)C=1C(=O)NCCCCC1=CC=CC=C1 VNUZXARZRWELJO-UHFFFAOYSA-N 0.000 claims description 2
- FTFBINRINIORBJ-UHFFFAOYSA-N 4-hydroxy-1-methyl-n-phenylindole-2-carboxamide Chemical compound C=1C2=C(O)C=CC=C2N(C)C=1C(=O)NC1=CC=CC=C1 FTFBINRINIORBJ-UHFFFAOYSA-N 0.000 claims description 2
- QTAABPDKPSKCNJ-UHFFFAOYSA-N 4-hydroxy-1-methylindole-2-carboxamide Chemical compound C1=CC=C2N(C)C(C(N)=O)=CC2=C1O QTAABPDKPSKCNJ-UHFFFAOYSA-N 0.000 claims description 2
- CKZLTECAOSGTBC-UHFFFAOYSA-N 4-hydroxy-1-methylindole-2-carboxylic acid Chemical compound C1=CC=C2N(C)C(C(O)=O)=CC2=C1O CKZLTECAOSGTBC-UHFFFAOYSA-N 0.000 claims description 2
- 206010027951 Mood swings Diseases 0.000 claims description 2
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- XRGYOXWBAUCLAX-AWEZNQCLSA-N diazonio-[(2s)-2-[(4-hydroxy-1-methylindole-2-carbonyl)amino]-3-phenylpropyl]azanide Chemical compound C([C@@H](CN=[N+]=[N-])NC(=O)C=1N(C2=CC=CC(O)=C2C=1)C)C1=CC=CC=C1 XRGYOXWBAUCLAX-AWEZNQCLSA-N 0.000 claims description 2
- 235000013305 food Nutrition 0.000 claims description 2
- HGHBXVSSWNDWGV-UHFFFAOYSA-N n-(1-fluoro-3-phenylpropan-2-yl)-4-hydroxy-1-methylindole-2-carboxamide Chemical compound C=1C2=C(O)C=CC=C2N(C)C=1C(=O)NC(CF)CC1=CC=CC=C1 HGHBXVSSWNDWGV-UHFFFAOYSA-N 0.000 claims description 2
- UWEAINNLPOKQDF-UHFFFAOYSA-N n-(2-fluoroethyl)-4-hydroxy-1-methylindole-2-carboxamide Chemical compound C1=CC=C2N(C)C(C(=O)NCCF)=CC2=C1O UWEAINNLPOKQDF-UHFFFAOYSA-N 0.000 claims description 2
- MPKQMEXBCWRJSI-UHFFFAOYSA-N n-(4-chlorophenyl)-4-hydroxy-1-methylindole-2-carboxamide Chemical compound C=1C2=C(O)C=CC=C2N(C)C=1C(=O)NC1=CC=C(Cl)C=C1 MPKQMEXBCWRJSI-UHFFFAOYSA-N 0.000 claims description 2
- VSDMPNPFAOTDRA-CQSZACIVSA-N n-[(2r)-2-fluoro-3-phenylpropyl]-4-hydroxy-1-methylindole-2-carboxamide Chemical compound C([C@@H](F)CNC(=O)C=1N(C2=CC=CC(O)=C2C=1)C)C1=CC=CC=C1 VSDMPNPFAOTDRA-CQSZACIVSA-N 0.000 claims description 2
- DISOOVOIBKFPCC-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-4-hydroxy-1-methylindole-2-carboxamide Chemical compound C=1C2=C(O)C=CC=C2N(C)C=1C(=O)NCC1=CC=C(Cl)C=C1 DISOOVOIBKFPCC-UHFFFAOYSA-N 0.000 claims description 2
- GDXAEGSNSMJISF-UHFFFAOYSA-N n-[[4-(dimethylamino)phenyl]methyl]-4-hydroxy-1-methylindole-2-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1CNC(=O)C1=CC2=C(O)C=CC=C2N1C GDXAEGSNSMJISF-UHFFFAOYSA-N 0.000 claims description 2
- NHZLWLAHJVXVQW-UHFFFAOYSA-N n-benzyl-4-hydroxy-1-methylindole-2-carboxamide Chemical compound C=1C2=C(O)C=CC=C2N(C)C=1C(=O)NCC1=CC=CC=C1 NHZLWLAHJVXVQW-UHFFFAOYSA-N 0.000 claims description 2
- JQKJBEJXYCWGPM-UHFFFAOYSA-N n-ethyl-4-hydroxy-1-methylindole-2-carboxamide Chemical compound C1=CC=C2N(C)C(C(=O)NCC)=CC2=C1O JQKJBEJXYCWGPM-UHFFFAOYSA-N 0.000 claims description 2
- 210000005036 nerve Anatomy 0.000 claims description 2
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- 206010009900 Colitis ulcerative Diseases 0.000 claims 6
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- 201000006704 Ulcerative Colitis Diseases 0.000 claims 6
- 210000000225 synapse Anatomy 0.000 claims 6
- 230000001713 cholinergic effect Effects 0.000 claims 5
- 208000015122 neurodegenerative disease Diseases 0.000 claims 4
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 3
- 230000009286 beneficial effect Effects 0.000 claims 3
- 208000028683 bipolar I disease Diseases 0.000 claims 3
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
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- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000004853 protein function Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 230000036390 resting membrane potential Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 238000010561 standard procedure Methods 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
- 239000008117 stearic acid Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000012581 transferrin Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000005500 uronium group Chemical group 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/22—Anxiolytics
-
- 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
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Psychology (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Indole Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9903998-4 | 1999-11-03 | ||
| SE9903998A SE9903998D0 (sv) | 1999-11-03 | 1999-11-03 | New compounds |
| PCT/SE2000/002147 WO2001032622A1 (en) | 1999-11-03 | 2000-11-01 | Positive modulators of nicotinic receptor agonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20020063175A true KR20020063175A (ko) | 2002-08-01 |
Family
ID=20417608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020027005705A Ceased KR20020063175A (ko) | 1999-11-03 | 2000-11-01 | 니코틴 수용체 작용물질의 양성 조절자 |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US7064143B1 (https=) |
| EP (1) | EP1230218A1 (https=) |
| JP (1) | JP2003513073A (https=) |
| KR (1) | KR20020063175A (https=) |
| CN (1) | CN1216864C (https=) |
| AU (1) | AU783602B2 (https=) |
| BR (1) | BR0015193A (https=) |
| CA (1) | CA2387741A1 (https=) |
| CO (1) | CO5280079A1 (https=) |
| IL (1) | IL149096A0 (https=) |
| MX (1) | MXPA02004240A (https=) |
| NO (1) | NO323077B1 (https=) |
| NZ (1) | NZ518449A (https=) |
| SE (1) | SE9903998D0 (https=) |
| WO (1) | WO2001032622A1 (https=) |
| ZA (1) | ZA200203181B (https=) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003039540A2 (en) * | 2001-11-09 | 2003-05-15 | Sepracor Inc. | D-amino acid oxidase inhibitors for learning and memory |
| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| GB0205165D0 (en) | 2002-03-06 | 2002-04-17 | Astrazeneca Ab | Chemical compounds |
| GB0205162D0 (en) | 2002-03-06 | 2002-04-17 | Astrazeneca Ab | Chemical compounds |
| GB0205166D0 (en) | 2002-03-06 | 2002-04-17 | Astrazeneca Ab | Chemical compounds |
| GB0205170D0 (en) | 2002-03-06 | 2002-04-17 | Astrazeneca Ab | Chemical compounds |
| GB0205175D0 (en) | 2002-03-06 | 2002-04-17 | Astrazeneca Ab | Chemical compounds |
| GB0205176D0 (en) | 2002-03-06 | 2002-04-17 | Astrazeneca Ab | Chemical compounds |
| JP2006501246A (ja) | 2002-08-30 | 2006-01-12 | メモリー・ファーマシューティカルズ・コーポレイション | 神経変性疾患の治療において有用なアナバセイン誘導体 |
| MXPA05003317A (es) | 2002-09-25 | 2005-07-05 | Memory Pharm Corp | Indazoles, benzotiazoles y benzoisotiazoles asi como preparacion y usos de los mismos. |
| GB0222912D0 (en) | 2002-10-03 | 2002-11-13 | Astrazeneca Ab | Novel process and intermediates |
| GB0222909D0 (en) | 2002-10-03 | 2002-11-13 | Astrazeneca Ab | Novel process and intermediates |
| US7405210B2 (en) | 2003-05-21 | 2008-07-29 | Osi Pharmaceuticals, Inc. | Pyrrolopyridine-2-carboxylic acid amide inhibitors of glycogen phosphorylase |
| JP2007517056A (ja) | 2003-12-29 | 2007-06-28 | セプラコア インコーポレーテッド | ピロール及びピラゾールｄａａｏ阻害剤 |
| JP2007527904A (ja) | 2004-03-08 | 2007-10-04 | プロシディオン・リミテッド | グリコーゲンホスホリラーゼ阻害剤としてのピロロピリジン−２−カルボン酸ヒドラジド化合物 |
| NZ550534A (en) | 2004-03-25 | 2009-07-31 | Memory Pharm Corp | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, and preparation and uses thereof |
| ES2340180T3 (es) | 2004-06-01 | 2010-05-31 | F.Hoffmann-La Roche Ag | 3-amino-1-arilpropil-indoles como inhibidores de reabsorcion de monoaminas. |
| JP5254616B2 (ja) | 2004-09-13 | 2013-08-07 | クロノ セラピューティクス、インコーポレイテッド | 生物学的同調性（ｂｉｏｓｙｎｃｈｒｏｎｏｕｓ）経皮的薬物送達 |
| US8252321B2 (en) | 2004-09-13 | 2012-08-28 | Chrono Therapeutics, Inc. | Biosynchronous transdermal drug delivery for longevity, anti-aging, fatigue management, obesity, weight loss, weight management, delivery of nutraceuticals, and the treatment of hyperglycemia, alzheimer's disease, sleep disorders, parkinson's disease, aids, epilepsy, attention deficit disorder, nicotine addiction, cancer, headache and pain control, asthma, angina, hypertension, depression, cold, flu and the like |
| US7223786B2 (en) | 2004-11-15 | 2007-05-29 | Bristol-Myers Squibb Company | 2-aminonaphthalene derivatives and related glycogen phosphorylase inhibitors |
| WO2006055462A1 (en) | 2004-11-15 | 2006-05-26 | Bristol-Myers Squibb Company | 2-amino-4-functionalized tetralin derivatives and related glycogen phosphorylase inhibitors |
| WO2006053274A2 (en) | 2004-11-15 | 2006-05-18 | Bristol-Myers Squibb Company | 2-amino-1-functionalized tetralin derivatives and related glycogen phosphorylase inhibitors |
| US7365061B2 (en) | 2004-11-15 | 2008-04-29 | Bristol-Myers Squibb Company | 2-Amino-3-functionalized tetralin derivatives and related glycogen phosphorylase inhibitors |
| ES2324173T3 (es) | 2004-12-02 | 2009-07-31 | Prosidion Limited | Amidas del acido pirrolopiridin-2-carboxilico. |
| FR2888847B1 (fr) | 2005-07-22 | 2007-08-31 | Sanofi Aventis Sa | Derives de n-(heteriaryl)-1-heteorarylalkyl-1h-indole-2- carboxamides, leur preparation et application en therapeutique |
| KR20080080593A (ko) | 2005-11-30 | 2008-09-04 | 에프. 호프만-라 로슈 아게 | 3-아미노-1-아릴프로필 인돌의 합성 방법 |
| ATE442368T1 (de) | 2005-11-30 | 2009-09-15 | Hoffmann La Roche | 3-amino-2-arylpropylazaindole und anwendungen davon |
| JP2009517430A (ja) | 2005-11-30 | 2009-04-30 | エフ．ホフマン−ラ ロシュ アーゲー | ３−アミノ−１−アリールプロピルインドール類及びアザ置換インドール類 |
| US7884124B2 (en) | 2006-06-30 | 2011-02-08 | Sepracor Inc. | Fluoro-substituted inhibitors of D-amino acid oxidase |
| MX2009007395A (es) * | 2007-01-09 | 2009-07-17 | Bayer Schering Pharma Ag | Marcacion radioactiva por fluoracion de aziridinas. |
| EP1944288A1 (en) * | 2007-01-09 | 2008-07-16 | Bayer Schering Pharma Aktiengesellschaft | Radiolabelling via fluorination of aziridines |
| EP2322168A1 (en) * | 2007-04-02 | 2011-05-18 | Parkinson's Institute | Methods and Compositions for Reduction of Side Effects of Therapeutic Treatments |
| US8383657B2 (en) | 2007-12-21 | 2013-02-26 | Abbott Laboratories | Thiazolylidine urea and amide derivatives and methods of use thereof |
| AR081402A1 (es) | 2010-05-17 | 2012-08-29 | Envivo Pharmaceuticals Inc | Una forma cristalina de clorhidrato de (r)-7-cloro-n-(quinuclidin-3-il) benzo(b)tiofeno-2-carboxamida monohidrato |
| AR085509A1 (es) | 2011-03-09 | 2013-10-09 | Bayer Cropscience Ag | Indol- y bencimidazolcarboxamidas como insecticidas y acaricidas |
| US20130017259A1 (en) | 2011-07-06 | 2013-01-17 | The Parkinson's Institute | Compositions and Methods for Treatment of Symptoms in Parkinson's Disease Patients |
| CA2872005A1 (en) | 2012-05-08 | 2013-11-14 | Forum Pharmaceuticals, Inc. | Methods of maintaining, treating or improving cognitive function |
| JP2018511355A (ja) | 2015-01-28 | 2018-04-26 | クロノ セラピューティクス インコーポレイテッドＣｈｒｏｎｏ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｉｎｃ． | 薬剤送達方法及びシステム |
| AU2016228779A1 (en) | 2015-03-12 | 2017-09-07 | Chrono Therapeutics Inc. | Craving input and support system |
| EP3565617A1 (en) | 2017-01-06 | 2019-11-13 | Chrono Therapeutics Inc. | Transdermal drug delivery devices and methods |
| EP3801732A4 (en) | 2018-05-29 | 2022-04-27 | Morningside Venture Investments Limited | METHODS AND SYSTEMS FOR DRUG DELIVERY |
| US12397141B2 (en) | 2018-11-16 | 2025-08-26 | Morningside Venture Investments Limited | Thermally regulated transdermal drug delivery system |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE758766A (fr) * | 1969-11-17 | 1971-05-10 | Ici Ltd | Nouveaux derives de la morpholine et de la |
| US4704390A (en) * | 1986-02-13 | 1987-11-03 | Warner-Lambert Company | Phenyl and heterocyclic tetrahydropyridyl alkoxy-benzheterocyclic compounds as antipsychotic agents |
| KR930702334A (ko) | 1990-09-13 | 1993-09-08 | 데이비드 로버트 | 5 하이드록시트립타민 수용체 길항제로서의 인돌우레아 |
| BR9206810A (pt) * | 1991-11-25 | 1995-10-31 | Pfizer | Derivados de indol |
| WO1993018026A1 (en) | 1992-03-04 | 1993-09-16 | Beecham Group Plc | Indole ureas as 5-ht1c receptor antogonists |
| US5504101A (en) | 1994-05-06 | 1996-04-02 | Allelix Biopharmaceuticals, Inc. | 5-HT-1D receptor ligands |
| FR2722686B1 (fr) * | 1994-07-22 | 1996-08-30 | Oreal | Set, procede, dispositif et composition de teinture des fibres keratiniques |
| US5576321A (en) * | 1995-01-17 | 1996-11-19 | Eli Lilly And Company | Compounds having effects on serotonin-related systems |
| SE9903997D0 (sv) * | 1999-11-03 | 1999-11-03 | Astra Ab | New compounds |
-
1999
- 1999-11-03 SE SE9903998A patent/SE9903998D0/xx unknown
-
2000
- 2000-11-01 KR KR1020027005705A patent/KR20020063175A/ko not_active Ceased
- 2000-11-01 AU AU14263/01A patent/AU783602B2/en not_active Ceased
- 2000-11-01 NZ NZ518449A patent/NZ518449A/en unknown
- 2000-11-01 CN CN008154406A patent/CN1216864C/zh not_active Expired - Fee Related
- 2000-11-01 BR BR0015193-9A patent/BR0015193A/pt not_active IP Right Cessation
- 2000-11-01 JP JP2001534774A patent/JP2003513073A/ja not_active Abandoned
- 2000-11-01 CA CA002387741A patent/CA2387741A1/en not_active Abandoned
- 2000-11-01 WO PCT/SE2000/002147 patent/WO2001032622A1/en not_active Ceased
- 2000-11-01 US US10/111,029 patent/US7064143B1/en not_active Expired - Fee Related
- 2000-11-01 EP EP00976499A patent/EP1230218A1/en not_active Withdrawn
- 2000-11-01 CO CO00083137A patent/CO5280079A1/es not_active Application Discontinuation
- 2000-11-01 MX MXPA02004240A patent/MXPA02004240A/es not_active Application Discontinuation
- 2000-11-01 IL IL14909600A patent/IL149096A0/xx unknown
-
2002
- 2002-04-22 ZA ZA200203181A patent/ZA200203181B/xx unknown
- 2002-05-02 NO NO20022105A patent/NO323077B1/no unknown
-
2005
- 2005-07-11 US US11/178,668 patent/US7402604B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| NO20022105L (no) | 2002-07-02 |
| CN1216864C (zh) | 2005-08-31 |
| JP2003513073A (ja) | 2003-04-08 |
| SE9903998D0 (sv) | 1999-11-03 |
| WO2001032622A1 (en) | 2001-05-10 |
| EP1230218A1 (en) | 2002-08-14 |
| US7064143B1 (en) | 2006-06-20 |
| US7402604B2 (en) | 2008-07-22 |
| IL149096A0 (en) | 2002-11-10 |
| ZA200203181B (en) | 2003-07-22 |
| CO5280079A1 (es) | 2003-05-30 |
| MXPA02004240A (es) | 2002-10-17 |
| NZ518449A (en) | 2004-07-30 |
| CN1387513A (zh) | 2002-12-25 |
| CA2387741A1 (en) | 2001-05-10 |
| BR0015193A (pt) | 2002-06-18 |
| NO323077B1 (no) | 2006-12-27 |
| US20050245595A1 (en) | 2005-11-03 |
| AU1426301A (en) | 2001-05-14 |
| NO20022105D0 (no) | 2002-05-02 |
| AU783602B2 (en) | 2005-11-10 |
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