SK2498A3 - Heterocyclylcarboxamide derivatives and their use as therapeutic agents - Google Patents
Heterocyclylcarboxamide derivatives and their use as therapeutic agents Download PDFInfo
- Publication number
- SK2498A3 SK2498A3 SK24-98A SK2498A SK2498A3 SK 2498 A3 SK2498 A3 SK 2498A3 SK 2498 A SK2498 A SK 2498A SK 2498 A3 SK2498 A3 SK 2498A3
- Authority
- SK
- Slovakia
- Prior art keywords
- benzodioxan
- ylmethyl
- methyl
- carboxamide
- pyridine
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims description 7
- 229940124597 therapeutic agent Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 269
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 40
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 11
- 206010020772 Hypertension Diseases 0.000 claims abstract description 11
- 208000018737 Parkinson disease Diseases 0.000 claims abstract description 11
- 208000028017 Psychotic disease Diseases 0.000 claims abstract description 11
- 208000000323 Tourette Syndrome Diseases 0.000 claims abstract description 11
- 208000016620 Tourette disease Diseases 0.000 claims abstract description 11
- 230000036506 anxiety Effects 0.000 claims abstract description 11
- 230000002526 effect on cardiovascular system Effects 0.000 claims abstract description 11
- 206010033664 Panic attack Diseases 0.000 claims abstract description 10
- 206010041250 Social phobia Diseases 0.000 claims abstract description 10
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 10
- 208000019906 panic disease Diseases 0.000 claims abstract description 10
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 10
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 9
- 208000026106 cerebrovascular disease Diseases 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 417
- 239000000203 mixture Substances 0.000 claims description 253
- 239000002904 solvent Substances 0.000 claims description 229
- -1 carbamoylmethyl Chemical group 0.000 claims description 113
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 111
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 100
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 66
- 125000004432 carbon atom Chemical group C* 0.000 claims description 59
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 59
- 239000011570 nicotinamide Substances 0.000 claims description 54
- 235000005152 nicotinamide Nutrition 0.000 claims description 54
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 51
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 50
- 229910052736 halogen Inorganic materials 0.000 claims description 46
- 150000002367 halogens Chemical class 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 21
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 11
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims 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 description 9
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 9
- 210000002307 prostate Anatomy 0.000 claims description 9
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 241000282414 Homo sapiens Species 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- 208000020401 Depressive disease Diseases 0.000 claims description 7
- 206010020880 Hypertrophy Diseases 0.000 claims description 7
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 7
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 239000007767 bonding agent Substances 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
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- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 3
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 claims description 3
- QQZCJIRWNDPUGX-UHFFFAOYSA-N 2-amino-n-[[1-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)piperidin-4-yl]methyl]pyridine-3-carboxamide Chemical compound NC1=NC=CC=C1C(=O)NCC1CCN(CC2OC3=CC=CC=C3OC2)CC1 QQZCJIRWNDPUGX-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- LZWZQYVPLLPAGX-UHFFFAOYSA-N 1h-pyrido[2,3-d][1,3]oxazine-2,4-dione Chemical compound C1=CC=C2C(=O)OC(=O)NC2=N1 LZWZQYVPLLPAGX-UHFFFAOYSA-N 0.000 claims description 2
- JELSQCUJCDGSPW-UHFFFAOYSA-N 2-amino-n-[[1-[(6-chloro-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]piperidin-4-yl]methyl]-6-methylpyridine-3-carboxamide Chemical compound NC1=NC(C)=CC=C1C(=O)NCC1CCN(CC2OC3=CC(Cl)=CC=C3OC2)CC1 JELSQCUJCDGSPW-UHFFFAOYSA-N 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 2
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- MSKHWAXYESDGKT-UHFFFAOYSA-N n-[[1-[[5-(trifluoromethyl)-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]piperidin-4-yl]methyl]pyridine-3-carboxamide Chemical compound O1C=2C(C(F)(F)F)=CC=CC=2OCC1CN(CC1)CCC1CNC(=O)C1=CC=CN=C1 MSKHWAXYESDGKT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
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- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 2
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- FARBJQYCWMFQND-SFHVURJKSA-N n-[[1-[[(3s)-6-fluoro-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]piperidin-4-yl]methyl]pyridine-3-carboxamide Chemical compound C([C@H]1COC2=CC=C(C=C2O1)F)N(CC1)CCC1CNC(=O)C1=CC=CN=C1 FARBJQYCWMFQND-SFHVURJKSA-N 0.000 description 1
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- LTEKQAPRXFBRNN-UHFFFAOYSA-N piperidin-4-ylmethanamine Chemical compound NCC1CCNCC1 LTEKQAPRXFBRNN-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
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- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
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- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
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- IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 1
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- QRDZFPUVLYEQTA-UHFFFAOYSA-N quinoline-8-carboxylic acid Chemical compound C1=CN=C2C(C(=O)O)=CC=CC2=C1 QRDZFPUVLYEQTA-UHFFFAOYSA-N 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 1
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- NZYFSKGFXHVPQG-UHFFFAOYSA-N tert-butyl 4-[[(2-methoxypyridine-3-carbonyl)amino]methyl]piperidine-1-carboxylate Chemical compound COC1=NC=CC=C1C(=O)NCC1CCN(C(=O)OC(C)(C)C)CC1 NZYFSKGFXHVPQG-UHFFFAOYSA-N 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
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
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- 230000007704 transition Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
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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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
-
- 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
-
- 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
-
- 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
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
- A61P25/18—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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Endocrinology (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Reproductive Health (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9514380.6A GB9514380D0 (en) | 1995-07-13 | 1995-07-13 | Therapeutic agents |
| PCT/EP1996/002890 WO1997003071A1 (en) | 1995-07-13 | 1996-07-02 | Heterocyclylcarboxamide derivatives and their use as therapeutic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK2498A3 true SK2498A3 (en) | 1998-09-09 |
Family
ID=10777626
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK24-98A SK2498A3 (en) | 1995-07-13 | 1996-07-02 | Heterocyclylcarboxamide derivatives and their use as therapeutic agents |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US5935973A (pt) |
| EP (1) | EP0839145B1 (pt) |
| JP (1) | JPH11508599A (pt) |
| KR (1) | KR19990028918A (pt) |
| CN (1) | CN1071755C (pt) |
| AT (1) | ATE253573T1 (pt) |
| AU (1) | AU708890B2 (pt) |
| BG (1) | BG62771B1 (pt) |
| BR (1) | BR9609506A (pt) |
| CA (1) | CA2223472A1 (pt) |
| CZ (1) | CZ388497A3 (pt) |
| DE (1) | DE69630604T2 (pt) |
| GB (1) | GB9514380D0 (pt) |
| HR (1) | HRP960348A2 (pt) |
| HU (1) | HUP9901485A3 (pt) |
| IL (1) | IL122540A (pt) |
| MX (1) | MX9800084A (pt) |
| NO (1) | NO980129D0 (pt) |
| NZ (1) | NZ313164A (pt) |
| PL (1) | PL324529A1 (pt) |
| RU (1) | RU2169147C2 (pt) |
| SK (1) | SK2498A3 (pt) |
| TR (1) | TR199800041T1 (pt) |
| TW (1) | TW454006B (pt) |
| WO (1) | WO1997003071A1 (pt) |
| ZA (1) | ZA965921B (pt) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9811879D0 (en) * | 1998-06-03 | 1998-07-29 | Knoll Ag | Therapeutic agents |
| GB9915616D0 (en) * | 1999-07-05 | 1999-09-01 | Knoll Ag | Therapeutic agents |
| UA73981C2 (en) | 2000-03-10 | 2005-10-17 | Merck Patent Gmbh | (r)-(-)-2-[5-(4-fluorophenyl)-3-pyridylmethylaminomethyl]-chromane for treatment of extrapyramidal movement disorders (variants), pharmaceutical composition and kit |
| WO2001078648A2 (en) * | 2000-04-17 | 2001-10-25 | Dong Wha Pharm. Ind. Co., Ltd. | 6-methylnicotinamide derivatives as antiviral agents |
| CA2428519A1 (en) * | 2000-11-14 | 2002-05-23 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Novel uses of combined selective dopamine d2 receptor antagonists and 5-ht1a receptor agonists |
| GB0112836D0 (en) | 2001-05-25 | 2001-07-18 | Smithkline Beecham Plc | Medicaments |
| US8106074B2 (en) | 2001-07-13 | 2012-01-31 | Pierre Fabre Medicament | Pyridin-2-yl-methylamine derivatives for treating opiate dependence |
| CN1292749C (zh) | 2001-07-26 | 2007-01-03 | 默克专利股份有限公司 | 2－[5－(4－氟苯基)－3－吡啶基甲氨基甲基]苯并二氢吡喃及其生理学上可接受的盐的新用途 |
| KR101204247B1 (ko) | 2003-07-22 | 2012-11-22 | 아스텍스 테라퓨틱스 리미티드 | 3,4-이치환된 1ｈ-피라졸 화합물 및 그의 시클린 의존성키나제 (ｃｄｋ) 및 글리코겐 합성효소 키나제-3(ｇｓｋ-3) 조정제로서 용도 |
| WO2005080394A1 (en) * | 2004-02-24 | 2005-09-01 | Bioaxone Therapeutique Inc. | 4-substituted piperidine derivatives |
| JP4604583B2 (ja) * | 2004-07-20 | 2011-01-05 | ダイソー株式会社 | １−アミド−３−（２−ヒドロキシフェノキシ）−２−プロパノール誘導体、ならびに２−アミドメチル−１，４−ベンゾジオキサン誘導体の製造法 |
| WO2006077424A1 (en) | 2005-01-21 | 2006-07-27 | Astex Therapeutics Limited | Pharmaceutical compounds |
| JP5475235B2 (ja) | 2005-01-21 | 2014-04-16 | アステックス・セラピューティクス・リミテッド | 医薬化合物 |
| TWI457122B (zh) | 2007-07-20 | 2014-10-21 | Orion Corp | 作為用於治療周邊和中央神經系統疾病之alpha2C拮抗劑的2,3－二氫苯並[1,4]戴奧辛－2－基甲基衍生物 |
| AU2009242092A1 (en) * | 2008-04-29 | 2009-11-05 | Nsab, Filial Af Neurosearch Sweden Ab, Sverige | Modulators of dopamine neurotransmission |
| MX356699B (es) * | 2012-06-11 | 2018-06-11 | Bristol Myers Squibb Co | Profarmacos de acido fosforamidico de 5-[5-fenil-4-(piridin-2-ilme tilamino) quinazolin-2-il]piridin-3-sulfonamida. |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8302622D0 (en) * | 1983-01-31 | 1983-03-02 | Celltech Ltd | Immunoassay |
| EP0200960A1 (en) * | 1985-05-08 | 1986-11-12 | Abbott Laboratories | Total estriol fluorescence polarization immunoassay |
| WO1991013872A1 (en) * | 1990-03-15 | 1991-09-19 | The Upjohn Company | Therapeutically useful heterocyclic indole compounds |
| US5240943A (en) * | 1991-12-19 | 1993-08-31 | G. D. Searle & Co. | Benzopyran class iii antiarrhythmic agents |
| GB9314758D0 (en) * | 1993-07-16 | 1993-08-25 | Wyeth John & Brother Ltd | Heterocyclic derivatives |
| GB9318431D0 (en) * | 1993-09-06 | 1993-10-20 | Boots Co Plc | Therapeutic agents |
| FR2724383B1 (fr) * | 1994-09-13 | 1996-10-18 | Synthelabo | Derives de 2-aminopyrimidine-4-carboxamide, leur preparation et leur application en therapeutique |
-
1995
- 1995-07-13 GB GBGB9514380.6A patent/GB9514380D0/en active Pending
-
1996
- 1996-07-02 SK SK24-98A patent/SK2498A3/sk unknown
- 1996-07-02 CZ CZ973884A patent/CZ388497A3/cs unknown
- 1996-07-02 IL IL12254096A patent/IL122540A/en not_active IP Right Cessation
- 1996-07-02 US US08/981,671 patent/US5935973A/en not_active Expired - Lifetime
- 1996-07-02 NZ NZ313164A patent/NZ313164A/xx unknown
- 1996-07-02 CN CN96195477A patent/CN1071755C/zh not_active Expired - Fee Related
- 1996-07-02 DE DE69630604T patent/DE69630604T2/de not_active Expired - Fee Related
- 1996-07-02 CA CA002223472A patent/CA2223472A1/en not_active Abandoned
- 1996-07-02 MX MX9800084A patent/MX9800084A/es not_active Application Discontinuation
- 1996-07-02 AU AU65172/96A patent/AU708890B2/en not_active Ceased
- 1996-07-02 AT AT96924847T patent/ATE253573T1/de not_active IP Right Cessation
- 1996-07-02 RU RU98102441/04A patent/RU2169147C2/ru active
- 1996-07-02 WO PCT/EP1996/002890 patent/WO1997003071A1/en not_active Application Discontinuation
- 1996-07-02 TR TR1998/00041T patent/TR199800041T1/xx unknown
- 1996-07-02 PL PL96324529A patent/PL324529A1/xx unknown
- 1996-07-02 JP JP9505471A patent/JPH11508599A/ja not_active Withdrawn
- 1996-07-02 BR BR9609506A patent/BR9609506A/pt unknown
- 1996-07-02 KR KR1019980700220A patent/KR19990028918A/ko not_active Application Discontinuation
- 1996-07-02 HU HU9901485A patent/HUP9901485A3/hu unknown
- 1996-07-02 EP EP96924847A patent/EP0839145B1/en not_active Expired - Lifetime
- 1996-07-12 HR HR9514380.6A patent/HRP960348A2/hr not_active Application Discontinuation
- 1996-07-12 ZA ZA9605921A patent/ZA965921B/xx unknown
- 1996-12-19 TW TW085115692A patent/TW454006B/zh not_active IP Right Cessation
-
1997
- 1997-12-23 BG BG102145A patent/BG62771B1/bg unknown
-
1998
- 1998-01-12 NO NO980129A patent/NO980129D0/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ313164A (en) | 1999-07-29 |
| HUP9901485A2 (en) | 2000-07-28 |
| HUP9901485A3 (en) | 2001-03-28 |
| EP0839145A1 (en) | 1998-05-06 |
| HRP960348A2 (en) | 1998-04-30 |
| IL122540A0 (en) | 1998-06-15 |
| IL122540A (en) | 2001-10-31 |
| US5935973A (en) | 1999-08-10 |
| CN1071755C (zh) | 2001-09-26 |
| TR199800041T1 (xx) | 1998-05-21 |
| DE69630604T2 (de) | 2004-09-23 |
| WO1997003071A1 (en) | 1997-01-30 |
| AU708890B2 (en) | 1999-08-12 |
| MX9800084A (es) | 1998-03-29 |
| CA2223472A1 (en) | 1997-01-30 |
| RU2169147C2 (ru) | 2001-06-20 |
| CZ388497A3 (cs) | 1998-06-17 |
| CN1190967A (zh) | 1998-08-19 |
| BR9609506A (pt) | 1999-06-01 |
| NO980129L (no) | 1998-01-12 |
| GB9514380D0 (en) | 1995-09-13 |
| ZA965921B (en) | 1998-01-12 |
| BG62771B1 (bg) | 2000-07-31 |
| TW454006B (en) | 2001-09-11 |
| BG102145A (en) | 1998-11-30 |
| KR19990028918A (ko) | 1999-04-15 |
| NO980129D0 (no) | 1998-01-12 |
| EP0839145B1 (en) | 2003-11-05 |
| ATE253573T1 (de) | 2003-11-15 |
| JPH11508599A (ja) | 1999-07-27 |
| AU6517296A (en) | 1997-02-10 |
| PL324529A1 (en) | 1998-06-08 |
| DE69630604D1 (de) | 2003-12-11 |
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