HRP990187A2 - Di-or triaza-spiro /4,5/decane derivatives - Google Patents
Di-or triaza-spiro /4,5/decane derivatives Download PDFInfo
- Publication number
- HRP990187A2 HRP990187A2 HR98110803.8A HRP990187A HRP990187A2 HR P990187 A2 HRP990187 A2 HR P990187A2 HR P990187 A HRP990187 A HR P990187A HR P990187 A2 HRP990187 A2 HR P990187A2
- Authority
- HR
- Croatia
- Prior art keywords
- phenyl
- spiro
- diaza
- decan
- cyclohexyl
- Prior art date
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- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical class CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 116
- 239000000203 mixture Substances 0.000 claims description 61
- -1 bicyclo[6.2.0]dec-9-yl Chemical group 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 108090000622 Nociceptin Proteins 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- PULGYDLMFSFVBL-SMFNREODSA-N nociceptin Chemical compound C([C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(O)=O)[C@@H](C)O)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 PULGYDLMFSFVBL-SMFNREODSA-N 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
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- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 230000001154 acute effect Effects 0.000 claims description 5
- 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 description 5
- 208000035475 disorder Diseases 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- 230000000926 neurological effect Effects 0.000 claims description 5
- UBBZCMHYEXFQLP-UHFFFAOYSA-N 8-(1,2,3,3a,4,5,6,7,8,8a-decahydroazulen-2-yl)-1-phenyl-1,8-diazaspiro[4.5]decan-4-ol Chemical compound C1CN(C2CC3CCCCCC3C2)CCC11C(O)CCN1C1=CC=CC=C1 UBBZCMHYEXFQLP-UHFFFAOYSA-N 0.000 claims description 4
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- PYLMXMMNCOOKBN-BGYRXZFFSA-N C1C[C@@H](C(C)C)CC[C@H]1N1CCC2(C(CCN2C=2C=CC=CC=2)=O)CC1 Chemical compound C1C[C@@H](C(C)C)CC[C@H]1N1CCC2(C(CCN2C=2C=CC=CC=2)=O)CC1 PYLMXMMNCOOKBN-BGYRXZFFSA-N 0.000 claims description 4
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- 208000000044 Amnesia Diseases 0.000 claims description 3
- ONQCLUYDCHVQHC-RLAPIPATSA-N C1C[C@@H](C(C)C)CC[C@H]1N1CCC2(N(CCC2O)C=2C=CC=CC=2)CC1 Chemical compound C1C[C@@H](C(C)C)CC[C@H]1N1CCC2(N(CCC2O)C=2C=CC=CC=2)CC1 ONQCLUYDCHVQHC-RLAPIPATSA-N 0.000 claims description 3
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 230000006984 memory degeneration Effects 0.000 claims description 3
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- 238000006268 reductive amination reaction Methods 0.000 claims description 3
- HLTDFERUYLFCNZ-UHFFFAOYSA-N 8-(2,3,3a,4,5,6,7,7a-octahydro-1h-inden-2-yl)-4-methoxy-1-phenyl-1,8-diazaspiro[4.5]decane Chemical compound C1CN(C2CC3CCCCC3C2)CCC11C(OC)CCN1C1=CC=CC=C1 HLTDFERUYLFCNZ-UHFFFAOYSA-N 0.000 claims description 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 description 2
- GSLQFTDIDMAQFF-TYABSZSSSA-N C1CN([C@H]2CC[C@H](CC2)C(C)C)CCC11C(OC)CCN1C1=CC=CC=C1 Chemical compound C1CN([C@H]2CC[C@H](CC2)C(C)C)CCC11C(OC)CCN1C1=CC=CC=C1 GSLQFTDIDMAQFF-TYABSZSSSA-N 0.000 claims description 2
- ONQCLUYDCHVQHC-VWPQPMDRSA-N C1C[C@@H](C(C)C)CC[C@H]1N1CCC2(N(CC[C@@H]2O)C=2C=CC=CC=2)CC1 Chemical compound C1C[C@@H](C(C)C)CC[C@H]1N1CCC2(N(CC[C@@H]2O)C=2C=CC=CC=2)CC1 ONQCLUYDCHVQHC-VWPQPMDRSA-N 0.000 claims description 2
- 125000004094 acenaphthen-1-yl group Chemical group [H]C1=C([H])C2=C3C(=C([H])C([H])=C([H])C3=C1[H])C([H])([H])C2([H])* 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 125000004129 indan-1-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])([H])C2([H])* 0.000 claims description 2
- 125000004130 indan-2-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])(*)C2([H])[H] 0.000 claims description 2
- 102000048266 Nociceptin Human genes 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 3
- ACUZDYFTRHEKOS-UHFFFAOYSA-N decan-2-ol Chemical compound CCCCCCCCC(C)O ACUZDYFTRHEKOS-UHFFFAOYSA-N 0.000 claims 1
- 206010013663 drug dependence Diseases 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 68
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 47
- 238000007429 general method Methods 0.000 description 44
- 239000007787 solid Substances 0.000 description 43
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
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- GPMJPYDKWWYFIF-UHFFFAOYSA-N 1-(2,3,3a,4,5,6-hexahydro-1h-phenalen-1-yl)piperidin-4-one Chemical compound C1CC(=O)CCN1C1C(C=CC=C2CCC3)=C2C3CC1 GPMJPYDKWWYFIF-UHFFFAOYSA-N 0.000 description 4
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- FYMLMIPDFQMCMX-UHFFFAOYSA-N 8-(1,2-dihydroacenaphthylen-1-yl)-1-phenyl-1,8-diazaspiro[4.5]decane-2,4-dione Chemical compound O=C1CC(=O)C2(CCN(CC2)C2C=3C=CC=C4C=CC=C(C=34)C2)N1C1=CC=CC=C1 FYMLMIPDFQMCMX-UHFFFAOYSA-N 0.000 description 4
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- 150000002825 nitriles Chemical class 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 230000003040 nociceptive effect Effects 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003399 opiate peptide Substances 0.000 description 1
- 239000008012 organic excipient Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002400 pro-nociceptive effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000002731 protein 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- CTDQAGUNKPRERK-UHFFFAOYSA-N spirodecane Chemical compound C1CCCC21CCCCC2 CTDQAGUNKPRERK-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- 238000010998 test method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- VMDMAAJZSXXCQV-UHFFFAOYSA-N trimethylsilylmethyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)COS(=O)(=O)C(F)(F)F VMDMAAJZSXXCQV-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom 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
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/24—Antidepressants
-
- 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
-
- 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
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/10—Spiro-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Child & Adolescent Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Photoreceptors In Electrophotography (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98110803 | 1998-06-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP990187A2 true HRP990187A2 (en) | 2000-02-29 |
Family
ID=8232113
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR98110803.8A HRP990187A2 (en) | 1998-06-12 | 1999-06-11 | Di-or triaza-spiro /4,5/decane derivatives |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US6642247B2 (de) |
| EP (1) | EP0963985B1 (de) |
| JP (1) | JP3369123B2 (de) |
| KR (1) | KR100393311B1 (de) |
| CN (2) | CN1110497C (de) |
| AR (1) | AR019860A1 (de) |
| AT (1) | ATE234302T1 (de) |
| AU (1) | AU752835B2 (de) |
| BR (1) | BR9902653A (de) |
| CA (1) | CA2274201C (de) |
| CO (1) | CO5040061A1 (de) |
| CZ (1) | CZ291323B6 (de) |
| DE (1) | DE69905798T2 (de) |
| DK (1) | DK0963985T3 (de) |
| ES (1) | ES2194402T3 (de) |
| HR (1) | HRP990187A2 (de) |
| HU (1) | HUP9901910A3 (de) |
| ID (1) | ID23306A (de) |
| IL (1) | IL130375A0 (de) |
| MA (1) | MA26645A1 (de) |
| NO (1) | NO312591B1 (de) |
| NZ (1) | NZ336226A (de) |
| PE (1) | PE20000540A1 (de) |
| PL (1) | PL333693A1 (de) |
| PT (1) | PT963985E (de) |
| SG (1) | SG83135A1 (de) |
| TR (1) | TR199901380A3 (de) |
| TW (1) | TW434241B (de) |
| YU (1) | YU26799A (de) |
| ZA (2) | ZA993853B (de) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0997464B1 (de) * | 1998-10-23 | 2005-02-16 | Pfizer Inc. | 1,3,8-Triazaspiro[4,5] decanon Verbindungen als orl1-receptor Agonisten |
| AU2003220886A1 (en) | 2002-03-29 | 2003-10-13 | Mitsubishi Pharma Corporation | Remedy for sleep disturbance |
| DE102004014296A1 (de) * | 2004-03-22 | 2005-10-06 | Grünenthal GmbH | Substituierte 1,4,8-Triazaspiro[4.5]decan-2-on-Verbindingen |
| KR100662191B1 (ko) | 2004-12-23 | 2006-12-27 | 엘지이노텍 주식회사 | 질화물 반도체 발광소자 및 그 제조방법 |
| ES2541133T3 (es) | 2007-03-01 | 2015-07-16 | Mitsubishi Tanabe Pharma Corporation | Compuesto de bencimidazol y uso farmacéutico del mismo |
| TW201016675A (en) | 2008-09-16 | 2010-05-01 | Mitsubishi Tanabe Pharma Corp | Crystalline benzoimidazole compound and salt thereof |
| CN109503582A (zh) * | 2018-12-17 | 2019-03-22 | 上海合全药物研发有限公司 | 顺式螺[哌啶并-4,1＇-吡咯并[3,4-c]吡咯]-1-甲酸叔丁酯的合成方法 |
| EP4137496A4 (de) * | 2020-05-12 | 2024-08-21 | Beijing Greatway Pharmaceutical Tech Co Ltd | Verbindung zur einstellung der aktivität des nmda-rezeptors sowie pharmazeutische zusammensetzung und verwendung davon |
| KR20220022988A (ko) | 2020-08-20 | 2022-03-02 | 제트스타 주식회사 | 트랙터용 써레 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63208844A (ja) * | 1987-02-26 | 1988-08-30 | Konica Corp | 有機着色物質の光褪色防止方法 |
| US5221675A (en) * | 1989-12-15 | 1993-06-22 | Abbott Laboratories | Aza-spirocyclic compounds that enhance cholinergic neurotransmission |
| US5534520A (en) * | 1990-04-10 | 1996-07-09 | Fisher; Abraham | Spiro compounds containing five-membered rings |
| CA2226058C (en) * | 1997-01-30 | 2008-01-29 | F. Hoffmann-La Roche Ag | 8-substituted-1,3,8-triaza-spiro[4.5]decan-4-one derivatives |
-
1999
- 1999-06-07 DE DE69905798T patent/DE69905798T2/de not_active Expired - Lifetime
- 1999-06-07 AT AT99110954T patent/ATE234302T1/de not_active IP Right Cessation
- 1999-06-07 DK DK99110954T patent/DK0963985T3/da active
- 1999-06-07 ES ES99110954T patent/ES2194402T3/es not_active Expired - Lifetime
- 1999-06-07 EP EP99110954A patent/EP0963985B1/de not_active Expired - Lifetime
- 1999-06-07 PT PT99110954T patent/PT963985E/pt unknown
- 1999-06-08 ZA ZA9903853A patent/ZA993853B/xx unknown
- 1999-06-08 CZ CZ19992039A patent/CZ291323B6/cs not_active IP Right Cessation
- 1999-06-08 PE PE1999000486A patent/PE20000540A1/es not_active Application Discontinuation
- 1999-06-09 IL IL13037599A patent/IL130375A0/xx unknown
- 1999-06-09 JP JP16194399A patent/JP3369123B2/ja not_active Expired - Fee Related
- 1999-06-09 HU HU9901910A patent/HUP9901910A3/hu unknown
- 1999-06-09 CA CA2274201A patent/CA2274201C/en not_active Expired - Fee Related
- 1999-06-09 SG SG9902947A patent/SG83135A1/en unknown
- 1999-06-10 AR ARP990102764A patent/AR019860A1/es active IP Right Grant
- 1999-06-10 CO CO99036580A patent/CO5040061A1/es unknown
- 1999-06-10 NZ NZ336226A patent/NZ336226A/xx unknown
- 1999-06-10 ZA ZA9903901A patent/ZA993901B/xx unknown
- 1999-06-10 MA MA25617A patent/MA26645A1/fr unknown
- 1999-06-10 AU AU34986/99A patent/AU752835B2/en not_active Ceased
- 1999-06-11 US US09/330,724 patent/US6642247B2/en not_active Expired - Fee Related
- 1999-06-11 HR HR98110803.8A patent/HRP990187A2/hr not_active Application Discontinuation
- 1999-06-11 TR TR1999/01380A patent/TR199901380A3/tr unknown
- 1999-06-11 NO NO19992876A patent/NO312591B1/no unknown
- 1999-06-11 BR BR9902653-8A patent/BR9902653A/pt active Search and Examination
- 1999-06-11 PL PL99333693A patent/PL333693A1/xx unknown
- 1999-06-11 CN CN99110904A patent/CN1110497C/zh not_active Expired - Fee Related
- 1999-06-11 YU YU26799A patent/YU26799A/sh unknown
- 1999-06-11 TW TW088109813A patent/TW434241B/zh not_active IP Right Cessation
- 1999-06-11 CN CNB991083741A patent/CN1229377C/zh not_active Expired - Fee Related
- 1999-06-12 KR KR10-1999-0021892A patent/KR100393311B1/ko not_active IP Right Cessation
- 1999-06-14 ID IDP990575D patent/ID23306A/id unknown
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