TW201132642A - Diaza-spiro[5.5]undecanes - Google Patents
Diaza-spiro[5.5]undecanes Download PDFInfo
- Publication number
- TW201132642A TW201132642A TW099144804A TW99144804A TW201132642A TW 201132642 A TW201132642 A TW 201132642A TW 099144804 A TW099144804 A TW 099144804A TW 99144804 A TW99144804 A TW 99144804A TW 201132642 A TW201132642 A TW 201132642A
- Authority
- TW
- Taiwan
- Prior art keywords
- methyl
- diazaspiro
- ring system
- undecane
- ketone
- Prior art date
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- XCRMJVAKOKRMRS-UHFFFAOYSA-N 1,2-diazaspiro[5.5]undecane Chemical class C1CCCCC21NNCCC2 XCRMJVAKOKRMRS-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 262
- 150000003839 salts Chemical group 0.000 claims abstract description 42
- 239000003814 drug Substances 0.000 claims abstract description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 295
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 226
- -1 aromatic oxime Chemical class 0.000 claims description 212
- 125000004122 cyclic group Chemical group 0.000 claims description 200
- 229910052757 nitrogen Inorganic materials 0.000 claims description 181
- 125000000217 alkyl group Chemical group 0.000 claims description 146
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 138
- 125000003118 aryl group Chemical group 0.000 claims description 116
- 150000002576 ketones Chemical class 0.000 claims description 109
- 125000001424 substituent group Chemical group 0.000 claims description 107
- 229910052760 oxygen Inorganic materials 0.000 claims description 101
- 239000001301 oxygen Substances 0.000 claims description 100
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 100
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 98
- 229910052736 halogen Inorganic materials 0.000 claims description 98
- 150000002367 halogens Chemical class 0.000 claims description 97
- 238000000034 method Methods 0.000 claims description 97
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 94
- 229910052717 sulfur Inorganic materials 0.000 claims description 94
- 125000005842 heteroatom Chemical group 0.000 claims description 91
- 239000011593 sulfur Substances 0.000 claims description 91
- 125000000623 heterocyclic group Chemical group 0.000 claims description 87
- 125000003545 alkoxy group Chemical group 0.000 claims description 73
- 125000004434 sulfur atom Chemical group 0.000 claims description 67
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 63
- 239000007789 gas Substances 0.000 claims description 58
- 239000000460 chlorine Substances 0.000 claims description 57
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 56
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 55
- 230000036528 appetite Effects 0.000 claims description 51
- 235000019789 appetite Nutrition 0.000 claims description 51
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 50
- 125000002950 monocyclic group Chemical group 0.000 claims description 49
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 47
- KMPQYAYAQWNLME-UHFFFAOYSA-N undecanal Chemical compound CCCCCCCCCCC=O KMPQYAYAQWNLME-UHFFFAOYSA-N 0.000 claims description 41
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 40
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 39
- 201000010099 disease Diseases 0.000 claims description 36
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 35
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 35
- VARQGBHBYZTYLJ-UHFFFAOYSA-N tricosan-12-one Chemical compound CCCCCCCCCCCC(=O)CCCCCCCCCCC VARQGBHBYZTYLJ-UHFFFAOYSA-N 0.000 claims description 32
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 125000002619 bicyclic group Chemical group 0.000 claims description 27
- 229920006395 saturated elastomer Polymers 0.000 claims description 27
- 238000011282 treatment Methods 0.000 claims description 26
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 25
- 125000001188 haloalkyl group Chemical group 0.000 claims description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- 125000006413 ring segment Chemical group 0.000 claims description 24
- 125000005605 benzo group Chemical group 0.000 claims description 22
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 22
- 108091008039 hormone receptors Proteins 0.000 claims description 21
- 125000001041 indolyl group Chemical group 0.000 claims description 19
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 18
- 239000011734 sodium Substances 0.000 claims description 18
- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims description 17
- 108020003175 receptors Proteins 0.000 claims description 17
- 102000005962 receptors Human genes 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 230000007958 sleep Effects 0.000 claims description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 13
- 208000024827 Alzheimer disease Diseases 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000002689 soil Substances 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 150000002923 oximes Chemical class 0.000 claims description 10
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 10
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 9
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 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 9
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Natural products C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 230000001404 mediated effect Effects 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 210000003802 sputum Anatomy 0.000 claims description 8
- 206010036790 Productive cough Diseases 0.000 claims description 7
- 208000024794 sputum Diseases 0.000 claims description 7
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 6
- 235000001258 Cinchona calisaya Nutrition 0.000 claims description 6
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims description 6
- 125000003367 polycyclic group Chemical group 0.000 claims description 6
- 229960000948 quinine Drugs 0.000 claims description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims description 6
- 208000030814 Eating disease Diseases 0.000 claims description 5
- 241000237858 Gastropoda Species 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 229940037003 alum Drugs 0.000 claims description 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 235000014632 disordered eating Nutrition 0.000 claims description 5
- 230000004630 mental health Effects 0.000 claims description 5
- 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
- 150000003852 triazoles Chemical class 0.000 claims description 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- ZAJNGDIORYACQU-UHFFFAOYSA-N methyl n-octyl ketone Natural products CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 claims description 4
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 4
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 claims description 3
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 3
- 125000004431 deuterium atom Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000000232 haloalkynyl 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
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- ROPLCSFPUPWHGJ-UHFFFAOYSA-N hydroxycyanamide Chemical compound ONC#N ROPLCSFPUPWHGJ-UHFFFAOYSA-N 0.000 claims description 3
- 241000894007 species Species 0.000 claims description 3
- LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 claims description 3
- UHFYTRKXKDDMME-UHFFFAOYSA-N 2,9-diazaspiro[5.5]undecan-1-one Chemical compound O=C1NCCCC11CCNCC1 UHFYTRKXKDDMME-UHFFFAOYSA-N 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- AGQOIYCTCOEHGR-UHFFFAOYSA-N 5-methyl-1,2-oxazole Chemical compound CC1=CC=NO1 AGQOIYCTCOEHGR-UHFFFAOYSA-N 0.000 claims description 2
- 101100074846 Caenorhabditis elegans lin-2 gene Proteins 0.000 claims description 2
- 101100497386 Mus musculus Cask gene Proteins 0.000 claims description 2
- 206010039424 Salivary hypersecretion Diseases 0.000 claims description 2
- 229910000831 Steel Inorganic materials 0.000 claims description 2
- 239000005864 Sulphur Chemical group 0.000 claims description 2
- 230000001055 chewing effect Effects 0.000 claims description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims description 2
- XUFQPHANEAPEMJ-UHFFFAOYSA-N famotidine Chemical compound NC(N)=NC1=NC(CSCCC(N)=NS(N)(=O)=O)=CS1 XUFQPHANEAPEMJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 2
- 210000003296 saliva Anatomy 0.000 claims description 2
- 208000026451 salivation Diseases 0.000 claims description 2
- 239000010959 steel Substances 0.000 claims description 2
- CCXHMPZXKYIXPU-UHFFFAOYSA-N undec-3-en-2-one Chemical compound CCCCCCCC=CC(C)=O CCXHMPZXKYIXPU-UHFFFAOYSA-N 0.000 claims description 2
- 235000001508 sulfur Nutrition 0.000 claims 19
- DOACSXJVHDTDSG-UHFFFAOYSA-N henicosan-11-one Chemical compound CCCCCCCCCCC(=O)CCCCCCCCCC DOACSXJVHDTDSG-UHFFFAOYSA-N 0.000 claims 2
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 claims 2
- YFKBXYGUSOXJGS-UHFFFAOYSA-N 1,3-Diphenyl-2-propanone Chemical compound C=1C=CC=CC=1CC(=O)CC1=CC=CC=C1 YFKBXYGUSOXJGS-UHFFFAOYSA-N 0.000 claims 1
- DUCJDCLFKLRRHZ-UHFFFAOYSA-N 1,3-benzothiazole-6-thiol Chemical compound SC1=CC=C2N=CSC2=C1 DUCJDCLFKLRRHZ-UHFFFAOYSA-N 0.000 claims 1
- ROVQEFKRZNILIZ-UHFFFAOYSA-N 1,9-diazaspiro[5.5]undecan-2-one Chemical compound N1C(=O)CCCC11CCNCC1 ROVQEFKRZNILIZ-UHFFFAOYSA-N 0.000 claims 1
- TWAVLAUIQVYLOR-UHFFFAOYSA-N 1-pyrrol-1-ylpyrrole Chemical group C1=CC=CN1N1C=CC=C1 TWAVLAUIQVYLOR-UHFFFAOYSA-N 0.000 claims 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- INQXGZFDGDSRIF-UHFFFAOYSA-N 1h-quinoxaline-2-thione Chemical compound C1=CC=CC2=NC(S)=CN=C21 INQXGZFDGDSRIF-UHFFFAOYSA-N 0.000 claims 1
- ABNXEGUBGHXRRQ-UHFFFAOYSA-N 2,9-diazaspiro[5.5]undecane Chemical compound C1CCNCC21CCNCC2 ABNXEGUBGHXRRQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- RQCBPOPQTLHDFC-UHFFFAOYSA-N 2-phenyl-1,3-oxazole Chemical compound C1=COC(C=2C=CC=CC=2)=N1 RQCBPOPQTLHDFC-UHFFFAOYSA-N 0.000 claims 1
- WPCSNGBKVXKBPU-UHFFFAOYSA-N 2-pyridin-3-yl-1,3-thiazole Chemical compound C1=CSC(C=2C=NC=CC=2)=N1 WPCSNGBKVXKBPU-UHFFFAOYSA-N 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 claims 1
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- 102000016736 Cyclin Human genes 0.000 claims 1
- 108050006400 Cyclin Proteins 0.000 claims 1
- VKJIVVDPXUBXKF-UHFFFAOYSA-N N=1C(C=C2C=CC=CC12)=O.C1NCCCC12CCNCC2 Chemical compound N=1C(C=C2C=CC=CC12)=O.C1NCCCC12CCNCC2 VKJIVVDPXUBXKF-UHFFFAOYSA-N 0.000 claims 1
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 1
- JDPQWHLMBJZURR-UHFFFAOYSA-N decan-5-one Chemical compound CCCCCC(=O)CCCC JDPQWHLMBJZURR-UHFFFAOYSA-N 0.000 claims 1
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims 1
- 238000010348 incorporation Methods 0.000 claims 1
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- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
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- 229930000223 plant secondary metabolite Natural products 0.000 claims 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
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- 125000003003 spiro group Chemical group 0.000 claims 1
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- 238000002360 preparation method Methods 0.000 abstract description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 285
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- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 91
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- 239000002253 acid Substances 0.000 description 19
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- 101150041968 CDC13 gene Proteins 0.000 description 14
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
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Classifications
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- 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
-
- 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
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- 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
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- 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
- A61P25/20—Hypnotics; Sedatives
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- 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
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- Chemical & Material Sciences (AREA)
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- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
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- General Chemical & Material Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- Pain & Pain Management (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| US20120101110A1 (en) * | 2010-10-26 | 2012-04-26 | Sangamesh Badiger | Diaza-spiro[5.5]undecanes |
| US20120165331A1 (en) * | 2010-12-22 | 2012-06-28 | Sangamesh Badiger | Di/tri-aza-spiro-C9-C11alkanes |
| JP6346862B2 (ja) | 2012-02-07 | 2018-06-20 | エオラス セラピューティクス， インコーポレイテッド | オレキシンレセプターアンタゴニストとしての置換プロリン／ピペリジン |
| US9440982B2 (en) | 2012-02-07 | 2016-09-13 | Eolas Therapeutics, Inc. | Substituted prolines/piperidines as orexin receptor antagonists |
| ITMI20120424A1 (it) | 2012-03-19 | 2013-09-20 | Rottapharm Spa | Composti chimici |
| WO2015113057A1 (en) * | 2014-01-27 | 2015-07-30 | Allergan, Inc. | Antagonists acting at multiple prostaglandin receptors for the treatment of inflammation |
| JP2017100951A (ja) * | 2014-04-04 | 2017-06-08 | 大正製薬株式会社 | オキサゾリジノン及びオキサジナノン誘導体 |
| TW201613902A (en) | 2014-08-13 | 2016-04-16 | Eolas Therapeutics Inc | Difluoropyrrolidines as orexin receptor modulators |
| US10196383B2 (en) | 2015-07-17 | 2019-02-05 | Sunshine Lake Pharma Co., Ltd. | Substituted quinazoline compounds and preparation and uses thereof |
| US10894789B2 (en) | 2016-02-12 | 2021-01-19 | Astrazeneca Ab | Halo-substituted piperidines as orexin receptor modulators |
| PE20190501A1 (es) | 2016-08-01 | 2019-04-10 | Aptinyx Inc | Moduladores nmda espiro-lactam y metodos de uso de los mismos |
| CA3031534C (en) | 2016-08-01 | 2023-10-17 | Aptinyx Inc. | Spiro-lactam nmda receptor modulators and uses thereof |
| EP3490992B1 (en) | 2016-08-01 | 2023-03-22 | Aptinyx Inc. | Spiro-lactam nmda receptor modulators and uses thereof |
| CN106831774B (zh) * | 2017-02-07 | 2019-02-01 | 上海合全药业股份有限公司 | 一种(6s，7s)-9-叔丁氧羰基-7-(三氟甲基)-2，9-二氮杂螺[5.5]十一烷的合成方法 |
| PE20210455A1 (es) | 2018-01-31 | 2021-03-08 | Aptinyx Inc | Moduladores del receptor nmda espiro-lactama y usos de los mismos |
| SG11202106108WA (en) * | 2019-01-28 | 2021-08-30 | Suntory Holdings Ltd | Composition for competitive inhibition of orexin receptors |
| UY39377A (es) | 2020-08-14 | 2022-03-31 | Novartis Ag | Derivados de espiropiperidinilo sustituidos con heteroarilo y usos farmacéuticos de los mismos |
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| AU2022376760A1 (en) * | 2021-10-27 | 2024-05-02 | Hansoh Bio Llc | Piperidinyl indole derivatives, preparation methods and medicinal uses thereof |
| US20240425519A1 (en) * | 2021-11-04 | 2024-12-26 | University Of Washington | Novel spirocyclic compounds as klhdc2 ligands |
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| PT72878B (en) | 1980-04-24 | 1983-03-29 | Merck & Co Inc | Process for preparing mannich-base hydroxamic acid pro-drugs for the improved delivery of non-steroidal anti-inflammatory agents |
| WO2004078163A2 (en) | 2003-02-28 | 2004-09-16 | Transform Pharmaceuticals, Inc. | Pharmaceutical co-crystal compositions of drugs such as carbamazepine, celecoxib, olanzapine, itraconazole, topiramate, modafinil, 5-fluorouracil, hydrochlorothiazide, acetaminophen, aspirin, flurbiprofen, phenytoin and ibuprofen |
| US7105526B2 (en) | 2002-06-28 | 2006-09-12 | Banyu Pharmaceuticals Co., Ltd. | Benzimidazole derivatives |
| JP4496722B2 (ja) * | 2002-06-28 | 2010-07-07 | 萬有製薬株式会社 | 新規ベンズイミダゾール誘導体 |
| JP2009506061A (ja) * | 2005-08-26 | 2009-02-12 | メルク エンド カムパニー インコーポレーテッド | ジアザスピロデカンオレキシン受容体拮抗薬 |
| PT1961744E (pt) * | 2005-11-18 | 2013-05-15 | Ono Pharmaceutical Co | Composto que contém um grupo básico e sua utilização |
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| US8530648B2 (en) | 2013-09-10 |
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| CN102762567A (zh) | 2012-10-31 |
| WO2011076747A1 (en) | 2011-06-30 |
| JP2013515033A (ja) | 2013-05-02 |
| AR079553A1 (es) | 2012-02-01 |
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