ME02606B - Jedinjenja 1,3 - oksazolidina ili 1,3- oksazinana kao antagonisti oreksinskog receptora - Google Patents
Jedinjenja 1,3 - oksazolidina ili 1,3- oksazinana kao antagonisti oreksinskog receptoraInfo
- Publication number
- ME02606B ME02606B MEP-2017-34A MEP201734A ME02606B ME 02606 B ME02606 B ME 02606B ME P201734 A MEP201734 A ME P201734A ME 02606 B ME02606 B ME 02606B
- Authority
- ME
- Montenegro
- Prior art keywords
- methyl
- methanone
- pyrazol
- phenyl
- triazol
- Prior art date
Links
- 150000001412 amines Chemical class 0.000 title 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 20
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- 125000001425 triazolyl group Chemical group 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 208000017701 Endocrine disease Diseases 0.000 claims 1
- 206010057615 Endocrine hypertension Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 1
- 206010019233 Headaches Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- DPVRTJAYOKJIFQ-ZHRRBRCNSA-N [(2s,4r)-2-[[3-(5-fluoropyridin-2-yl)pyrazol-1-yl]methyl]-4-methyl-1,3-oxazolidin-3-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1OC[C@H](N1C(=O)C=1C(=CC=C(C)C=1)N1N=CC=N1)C)N(N=1)C=CC=1C1=CC=C(F)C=N1 DPVRTJAYOKJIFQ-ZHRRBRCNSA-N 0.000 claims 1
- DPVRTJAYOKJIFQ-AOMKIAJQSA-N [(2s,4s)-2-[[3-(5-fluoropyridin-2-yl)pyrazol-1-yl]methyl]-4-methyl-1,3-oxazolidin-3-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1OC[C@@H](N1C(=O)C=1C(=CC=C(C)C=1)N1N=CC=N1)C)N(N=1)C=CC=1C1=CC=C(F)C=N1 DPVRTJAYOKJIFQ-AOMKIAJQSA-N 0.000 claims 1
- XIJFGHZYWVCPFJ-ZHRRBRCNSA-N [(2s,5r)-2-[[4-(5-fluoropyridin-2-yl)pyrazol-1-yl]methyl]-5-methyl-1,3-oxazolidin-3-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1N(C[C@H](O1)C)C(=O)C=1C(=CC=C(C)C=1)N1N=CC=N1)N(N=C1)C=C1C1=CC=C(F)C=N1 XIJFGHZYWVCPFJ-ZHRRBRCNSA-N 0.000 claims 1
- XIJFGHZYWVCPFJ-AOMKIAJQSA-N [(2s,5s)-2-[[4-(5-fluoropyridin-2-yl)pyrazol-1-yl]methyl]-5-methyl-1,3-oxazolidin-3-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1N(C[C@@H](O1)C)C(=O)C=1C(=CC=C(C)C=1)N1N=CC=N1)N(N=C1)C=C1C1=CC=C(F)C=N1 XIJFGHZYWVCPFJ-AOMKIAJQSA-N 0.000 claims 1
- HVYGOEAVNOYJPX-UHFFFAOYSA-N [2-[[1-(5-fluoropyridin-2-yl)pyrazol-4-yl]methyl]-1,3-oxazinan-3-yl]-(5-fluoro-2-pyrimidin-2-ylphenyl)methanone Chemical compound Fc1ccc(nc1)-n1cc(CC2OCCCN2C(=O)c2cc(F)ccc2-c2ncccn2)cn1 HVYGOEAVNOYJPX-UHFFFAOYSA-N 0.000 claims 1
- GJIDHTCQPKWTIL-UHFFFAOYSA-N [2-[[1-(5-fluoropyridin-2-yl)pyrazol-4-yl]methyl]-1,3-oxazinan-3-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound Cc1ccc(c(c1)C(=O)N1CCCOC1Cc1cnn(c1)-c1ccc(F)cn1)-n1nccn1 GJIDHTCQPKWTIL-UHFFFAOYSA-N 0.000 claims 1
- NCKZYCBDYGDFRC-UHFFFAOYSA-N [2-[[1-(5-fluoropyridin-2-yl)pyrazol-4-yl]methyl]-1,3-oxazolidin-3-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound Cc1ccc(c(c1)C(=O)N1CCOC1Cc1cnn(c1)-c1ccc(F)cn1)-n1nccn1 NCKZYCBDYGDFRC-UHFFFAOYSA-N 0.000 claims 1
- LRBYYJMSSHIJKG-UHFFFAOYSA-N [2-[[3-(4-fluorophenyl)pyrazol-1-yl]methyl]-1,3-oxazinan-3-yl]-(5-methyl-2-pyrimidin-2-ylphenyl)methanone Chemical compound Cc1ccc(c(c1)C(=O)N1CCCOC1Cn1ccc(n1)-c1ccc(F)cc1)-c1ncccn1 LRBYYJMSSHIJKG-UHFFFAOYSA-N 0.000 claims 1
- XMTCRKRHFLBROW-UHFFFAOYSA-N [2-[[3-(4-fluorophenyl)pyrazol-1-yl]methyl]-1,3-oxazinan-3-yl]-(6-methyl-3-pyrimidin-2-ylpyridin-2-yl)methanone Chemical compound C1CCOC(CN2N=C(C=C2)C=2C=CC(F)=CC=2)N1C(=O)C1=NC(C)=CC=C1C1=NC=CC=N1 XMTCRKRHFLBROW-UHFFFAOYSA-N 0.000 claims 1
- YZRHBGIKWQSFJJ-UHFFFAOYSA-N [2-[[3-(5-fluoropyridin-2-yl)pyrazol-1-yl]methyl]-1,3-oxazinan-3-yl]-(5-fluoro-2-pyrimidin-2-ylphenyl)methanone Chemical compound N1=CC(F)=CC=C1C1=NN(CC2N(CCCO2)C(=O)C=2C(=CC=C(F)C=2)C=2N=CC=CN=2)C=C1 YZRHBGIKWQSFJJ-UHFFFAOYSA-N 0.000 claims 1
- REIHLDGDOFIXTP-UHFFFAOYSA-N [2-[[3-(5-fluoropyridin-2-yl)pyrazol-1-yl]methyl]-1,3-oxazinan-3-yl]-(5-methyl-2-pyrimidin-2-ylphenyl)methanone Chemical compound Cc1ccc(c(c1)C(=O)N1CCCOC1Cn1ccc(n1)-c1ccc(F)cn1)-c1ncccn1 REIHLDGDOFIXTP-UHFFFAOYSA-N 0.000 claims 1
- SEIYMHWXOQHIRD-UHFFFAOYSA-N [2-[[3-(5-fluoropyridin-2-yl)pyrazol-1-yl]methyl]-1,3-oxazinan-3-yl]-[5-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound Fc1ccc(nc1)-c1ccn(CC2OCCCN2C(=O)c2cc(F)ccc2-n2nccn2)n1 SEIYMHWXOQHIRD-UHFFFAOYSA-N 0.000 claims 1
- AEZZJXJIJFSUEM-UHFFFAOYSA-N [2-[[3-(5-fluoropyridin-2-yl)pyrazol-1-yl]methyl]-1,3-oxazinan-3-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C=1C(C)=CC=C(N2N=CC=N2)C=1C(=O)N1CCCOC1CN(N=1)C=CC=1C1=CC=C(F)C=N1 AEZZJXJIJFSUEM-UHFFFAOYSA-N 0.000 claims 1
- LHSPBVKFWDHYSG-UHFFFAOYSA-N [2-[[4-(4-fluorophenyl)pyrazol-1-yl]methyl]-1,3-oxazinan-3-yl]-(5-methyl-2-pyrimidin-2-ylphenyl)methanone Chemical compound Cc1ccc(c(c1)C(=O)N1CCCOC1Cn1cc(cn1)-c1ccc(F)cc1)-c1ncccn1 LHSPBVKFWDHYSG-UHFFFAOYSA-N 0.000 claims 1
- XZALYTFRMPIXPU-UHFFFAOYSA-N [2-[[4-(4-fluorophenyl)pyrazol-1-yl]methyl]-1,3-oxazinan-3-yl]-(6-methyl-3-pyrimidin-2-ylpyridin-2-yl)methanone Chemical compound C1CCOC(CN2N=CC(=C2)C=2C=CC(F)=CC=2)N1C(=O)C1=NC(C)=CC=C1C1=NC=CC=N1 XZALYTFRMPIXPU-UHFFFAOYSA-N 0.000 claims 1
- AQFPGDOPAWNDQW-UHFFFAOYSA-N [2-[[4-(4-fluorophenyl)pyrazol-1-yl]methyl]-1,3-oxazinan-3-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C=1C(C)=CC=C(N2N=CC=N2)C=1C(=O)N1CCCOC1CN(N=C1)C=C1C1=CC=C(F)C=C1 AQFPGDOPAWNDQW-UHFFFAOYSA-N 0.000 claims 1
- QUYOMENBDKOHHU-UHFFFAOYSA-N [2-[[4-(5-fluoropyridin-2-yl)pyrazol-1-yl]methyl]-1,3-oxazolidin-3-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C=1C(C)=CC=C(N2N=CC=N2)C=1C(=O)N1CCOC1CN(N=C1)C=C1C1=CC=C(F)C=N1 QUYOMENBDKOHHU-UHFFFAOYSA-N 0.000 claims 1
- XIBNNBMLUUIACY-UHFFFAOYSA-N [2-[[5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl]methyl]-1,3-oxazinan-3-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C=1C(C)=CC=C(N2N=CC=N2)C=1C(=O)N1CCCOC1CC(N=1)=NOC=1C1=CC=C(F)C=C1 XIBNNBMLUUIACY-UHFFFAOYSA-N 0.000 claims 1
- ABQUTJKCXJRSSO-UHFFFAOYSA-N [2-[[5-(4-fluorophenyl)-1,2,4-oxadiazol-3-yl]methyl]-1,3-oxazinan-3-yl]-[6-methyl-3-(triazol-2-yl)pyridin-2-yl]methanone Chemical compound N=1C(C)=CC=C(N2N=CC=N2)C=1C(=O)N1CCCOC1CC(N=1)=NOC=1C1=CC=C(F)C=C1 ABQUTJKCXJRSSO-UHFFFAOYSA-N 0.000 claims 1
- HCUREBSNYDMSKO-UHFFFAOYSA-N [2-[[5-(5-fluoropyridin-2-yl)-1,2,4-oxadiazol-3-yl]methyl]-1,3-oxazinan-3-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C=1C(C)=CC=C(N2N=CC=N2)C=1C(=O)N1CCCOC1CC(N=1)=NOC=1C1=CC=C(F)C=N1 HCUREBSNYDMSKO-UHFFFAOYSA-N 0.000 claims 1
- 239000013626 chemical specie Substances 0.000 claims 1
- 208000010643 digestive system disease Diseases 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 235000014632 disordered eating Nutrition 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 206010013663 drug dependence Diseases 0.000 claims 1
- 208000030172 endocrine system disease Diseases 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 208000018685 gastrointestinal system disease Diseases 0.000 claims 1
- 231100000869 headache Toxicity 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 208000019906 panic disease Diseases 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 208000019116 sleep disease Diseases 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Classifications
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- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
-
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- 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5355—Non-condensed oxazines and containing further heterocyclic rings
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- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Psychology (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Addiction (AREA)
- Child & Adolescent Psychology (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Claims (9)
1. Jedinjenje predstavljeno formulom (IA): naznačeno time što su X1 i X2 isti ili različiti i predstavljaju atom azota ili formulu CH; Y predstavlja bilo koju od struktura u sledećoj grupi formula (a): n predstavlja 1 ili 2; R1 predstavlja atom vodonika, halogeni atom ili C1-6 alkil grupu; R2 predstavlja triazolil grupu, piridil grupu ili pirimidinil grupu; R3 predstavlja atom vodonika, halogeni atom ili C1-6 alkil grupu, gde navedena C1-6 alkil grupa može opciono da bude supstituisana sa 1 do 3 halogena atoma; a R4 predstavlja vodonikov atom ili C1-6 alkil grupu; ili farmaceutski prihvatljiva so takvog jedinjenja.
2. Jedinjenje ili farmaceutski prihvatljiva so takvog jedinjenja prema patentnom zahtevu 1, naznačena time što u prethodnoj formuli (IA), R2 jeste triazolil grupa ili pirimidinil grupa a R3 jeste halogeni atom.
3. Jedinjenje ili farmaceutski prihvatljiva so takvog jedinjenja prema patentnim zahtevima 1 ili 2, naznačeno time što u prethodnoj formuli (IA) n jeste 2.
4. Jedinjenje ili farmaceutski prihvatljiva so takvog jedinjenja prema patentnom zahtevu 1, naznačeno time što je dato jedinjenje predstavljeno formulom (I): gde X1 i X2 jesu isti ili različiti i predstavljaju atom azota ili formulu CH; bilo koji od Y1 i Y2 predstavlja atom azota, a drugi predstavlja CH; n predstavlja 1 ili 2; R1 predstavlja vodonikov atom, halogeni atom ili C1-6 alkil grupu; R2 predstavlja triazolil grupu, piridil grupu ili pirimidinil grupu; R3 predstavlja atom vodonika, halogeni atom ili C1-6 alkil grupu, gde navedena C1-6 alkil grupa može opciono da bude supstituisana sa 1 do 3 halogena atoma; a R4 predstavlja vodonikov atom ili C1-6 alkil grupu; ili farmaceutski prihvatljiva so takvog jedinjenja.
5. Jedinjenje ili farmaceutski prihvatljiva so takvog jedinjenja prema patentnom zahtevu 4, naznačena time što u prethodnoj formuli (I), R2 jeste triazolil grupa ili pirimidinil grupa; a R3 jeste halogeni atom.
6. Jedinjenje ili farmaceutski prihvatljiva so takvog jedinjenja prema patentnim zahtevima 4 ili 5, naznačeno time što u prethodnoj formuli (I) n jeste 2.
7. Jedinjenje ili farmaceutski prihvatljiva so takvog jedinjenja prema patentnom zahtevu 1, naznačeno time da predstavlja hemijsku vrstu, ili smešu više vrsta, izabranih iz grupe koja se sastoji od: (-)-(2-{[3-(5-fluorpiridin-2-il)-1H-pirazol-1-il]metil}-1,3-oksazolidin-3-il)[5-metil-2-(2H-1,2,3-triazol-2-il)fenil]metanona, (-)-(2-{[4-(5-fluorpiridin-2-il)-1H-pirazol-1-il]metil}-1,3-oksazolidin-3-il)[5-metil-2-(2H-1,2,3-triazol-2-il)fenil]metanona, (-)-(2-{[3-(5-fluorpiridin-2-il)-1H-pirazol-1-il]metil}-1,3-oksazinan-3-il)[5-metil-2-(2H-1,2,3-triazol-2-il)fenil]metanona, (-)-(2-{[4-(5-fluorpiridin-2-il)-1H-pirazol-1-il]metil}-1,3-oksazinan-3-il)[5-metil-2-(2H-1,2,3-triazol-2-il)fenil]metanona, (-)-[(2S,5S)-2-{[4-(5-fluorpiridin-2-il)-1H-pirazol-1-il]metil}-5-metil-1,3-oksazolidin-3-il][5-metil-2-(2H-1,2,3-triazol-2-il)fenil]metanona, (-)-[(2S,5R)-2-{[4-(5-fluorpiridin-2-il)-1H-pirazol-1-il]metil}-5-metil-1,3-oksazolidin-3-il][5-metil-2-(2H-1,2,3-triazol-2-il)fenil]metanona, [(2S,4R)-2-{[3-(5-fluorpiridin-2-il)-1H-pirazol-1-il]metil}-4-metil-1,3-oksazolidin-3-il][5-metil-2-(2H-1,2,3-triazol-2-il)fenil]metanona, (-)-[(2S,4S)-2-{[3-(5-fluorpiridin-2-il)-1H-pirazol-1-il]metil}-4-metil-1,3-oksazolidin-3-il][5-metil-2-(2H-1,2,3-triazol-2-il)fenil]metanona, (6)-2-{[3-(5-fluorpiridin-2-il)-1H-pirazol-1-il]metil}-1,3-oksazolidin-3-il][5-metil-2-(pirimidin-2-il)fenil]metanona, (6)-(2-{[3-(5-fluorpiridin-2-il)-1H-pirazol-1-il]metil}-1,3-oksazolidin-3-il)[5-fluor-2-(pirimidin-2-il)fenil]metanona, (6)-(2-{[3-(4-fluorfenil)-1H-pirazol-1-il]metil}-1,3-oksazolidin-3-il)[5-metil-2-(2H-1,2,3-triazol-2-il)fenil]metanona, (6)-(2-{[4-(4-fluorfenil)-1H-pirazol-1-il]metil}-1,3-oksazolidin-3-il)[5-metil-2-(2H-1,2,3-triazol-2-il)fenil]metanona, (6)-(2-{[4-(4-fluorfenil)-1H-pirazol-1-il]metil}-1,3-oksazolidin-3-il)[5-metil-2-(pirimidin-2-il)fenil]metanona, (-)-(2-{{[3-(4-fluorfenil)-1H-pirazol-1-il]metil}-1,3-oksazolidin-3-il)[6-metil-3-(2H-1,2,3-triazol-2-il)piridin-2-il]metanona, (-)-(2-{[3-(4-fluorfenil)-1H-pirazol-1-il]metil}-1,3-oksazinan-3-il)[6-metil-3-(2H-1,2,3-triazol-2-il)piridin-2-il]metanona, (-)-(2-{[3-(4-fluorfenil)-1H-pirazol-1-il]metil}-1,3-oksazinan-3-il)[6-metil-3-(pirimidin-2-il)piridin-2-il]metanona, (-)-(2-{[3-(5-fluorpiridin-2-il)-1H-pirazol-1-il]metil}-1,3-oksazinan-3-il)[5-fluor-2-(2H-1,2,3-triazol-2-il)fenil]metanona, (-)-(2-{[3-(5-fluorpiridin-2-il)-1H-pirazol-1-il]metil}-1,3-oksazinan-3-il)[5-metil-2-(pirimidin-2-il)fenil]metanona, (-)-(2-{[4-(4-fluorfenil)-1H-pirazol-1-il]metil}-1,3-oksazinan-3-il)[6-metil-3-(2H-1,2,3-triazol-2-il)piridin-2-il]metanona, (-)-(2-{[4-(4-fluorfenil)-1H-pirazol-1-il]metil}-1,3-oksazinan-3-il)[6-metil-3-(pirimidin-2-il)piridin-2-il]metanona, (-)-[2-{[3-(5-fluorpiridin-2-il)-1H-pirazol-1-il]metil}-1,3-oksazinan-3-il][5-fluor-2-(pirimidin-2-il)fenil]metanona, (-)-[2-{[4-(4-fluorfenil)-1H-pirazol-1-il]metil}-1,3-oksazinan-3-il][5-metil-2-(2H-1,2,3-triazol-2-il)fenil]metanona, (-)-[2-{[5-(5-fluorpiridin-2-il)-1,2,4-oksadiazol-3-il]metil}-1,3-oksazinan-3-il][5-metil-2-(2H-1,2,3-triazol-2-il)fenil]metanona, (-)-[2-{[5-(4-fluorfenil)-1,2,4-oksadiazol-3-il]metil}-1,3-oksazinan-3-il][5-metil-2-(2H-1,2,3-triazol-2-il)fenil]metanona, (-)-[2-{[5-(4-fluorfenil)-1,2,4-oksadiazol-3-il]metil}-1,3-oksazinan-3-il][6-metil-3-(2H-1,2,3-triazol-2-il)piridin-2-il]metanona, [(2S,4S)-2-{[4-(5-fluorpiridin-2-il)-1H-pirazol-1-il]metil}-4-metil-1,3-oksazinan-3-il[5-metil-2-(2H-1,2,3-triazol-2-il)fenil]metanona, (-)-[(2S*,5S*)-2-{[4-(5-fluorpiridin-2-il)-1H-pirazol-1-il]metil}-5-metil-1,3-oksazinan-3-il][5-metil-2-(2H-1,2,3-triazol-2-il)fenil]metanona, (-)-[2-{[3-(4-fluorfenil)-1H-pirazol-1-il]metil}-1,3-oksazinan-3-il][5-metil-2-(pirimidin-2-il)fenil]metanona, (6)-[2-{[1-(5-fluorpiridin-2-il)-1H-pirazol-4-il]metil}-1,3-oksazinan-3-il][5-metil-2-(pirimidin-2-il)fenil]metanona, (-)-[2-{[4-(4-fluorfenil)-1H-pirazol-1-il]metil}-1,3-oksazinan-3-il][5-metil-2-(pirimidin-2-il)fenil]metanona, (-)-[2-{[1-(5-fluorpiridin-2-il)-1H-pirazol-4-il]metil}-1,3-oksazinan-3-il][5-fluor-2-(pirimidin-2-il)fenil]metanona, (-)-[2-[1-(5-fluorpiridin-2-il)-1H-pirazol-3-il]metil}-1,3-oksazolidin-3-il][5-metil-2-(2H-1,2,3-triazol-2-il)fenil]metanona, (-)-[2-{[1-(5-fluorpiridin-2-il)-1H-pirazol-4-il]metil}-1,3-oksazolidin-3-il][5-metil-2-(2H-1,2,3-triazol-2-il)fenil]metanona, (-)-[2-{[1-(5-fluorpiridin-2-il)-1H-pirazol-4-il]metil}-1,3-oksazinan-3-il][5-metil-2-(2H-1,2,3-triazol-2-il)fenil]metanona, (-)-[(2S*,5R*)-2-{[4-(5-fluorpiridin-2-il)-1H-pirazol-1-il]metil}-5-metil-1,3-oksazinan-3-il][5-metil-2-(2H-1,2,3-triazol-2-il)fenil]metanona.
8. Farmaceutski preparat naznačen time što sadrži jedinjenje, ili farmaceutski prihvatljivu so takvog jedinjenja iz bilo kog od patentnih zahteva 1 do 7, kao aktivni sastojak.
9. Lek naznačen time što sadrži jedinjenje, ili farmaceutski prihvatljivu so takvog jedinjenja iz bilo kog od patentnih zahteva 1 do 7 kao aktivni sastojak za upotrebu u terapiji ili prevenciji bolesti kao što su poremećaji sna, depresija, anksiozni poremećaj, panični poremećaj, šizofrenija, zavisnost od droga, Alchajmerova bolest, Parkinsonova bolest, Hantingtonova bolest, poremećaji ishrane, glavobolja, migrena, bol, gastrointestinalna bolest, epilepsija, zapaljenje, imunološka bolest, endokrine bolesti ili hipertenzija.
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| PCT/JP2013/066322 WO2013187467A1 (ja) | 2012-06-15 | 2013-06-13 | ヘテロ芳香環メチル環状アミン誘導体 |
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| KR101859409B1 (ko) | 2009-10-23 | 2018-05-18 | 얀센 파마슈티카 엔.브이. | 오렉신 수용체 조절제로서의 이치환된 옥타하이드로피롤로［3,4-ｃ］피롤 |
| JP2017024990A (ja) * | 2013-12-13 | 2017-02-02 | 大正製薬株式会社 | オキサゾリジン及びオキサジナン誘導体 |
| JP5907310B2 (ja) * | 2013-12-13 | 2016-04-26 | 大正製薬株式会社 | オキサジナン化合物の結晶形及びその製造方法 |
| CN104370755B (zh) * | 2014-08-18 | 2017-04-12 | 江西隆莱生物制药有限公司 | 一种光学活性的3‑氨基丁醇和3‑氨基丁酸的制备方法 |
| JP2018188364A (ja) * | 2015-10-02 | 2018-11-29 | 大正製薬株式会社 | 複素芳香環誘導体 |
| PT3426251T (pt) | 2016-03-10 | 2022-07-27 | Janssen Pharmaceutica Nv | Métodos de tratamento da depressão utilizando antagonistas dos recetores de orexina-2 |
| CN108129426B (zh) * | 2016-12-01 | 2021-06-29 | 中国科学院大连化学物理研究所 | 一种2,5-二氰基呋喃催化加氢合成2,5-二甲胺基呋喃的方法 |
| JOP20190156B1 (ar) * | 2016-12-23 | 2023-09-17 | Bayer Pharma AG | أميدات عطرية لحمض الكربوكسيليك بصفتها مضادات لمستقبلة البراديكينين b1 |
| CN110869368B (zh) * | 2017-07-13 | 2023-03-28 | 大正制药株式会社 | （2s）-2-［（1h-吡唑-1-基）甲基］-1,3-噁嗪烷衍生物的制备方法 |
| CN110967321A (zh) * | 2018-09-29 | 2020-04-07 | 泰州医药城国科化物生物医药科技有限公司 | 一种用于均一体系细胞荧光检测钙流方法 |
| CA3184307A1 (en) | 2020-05-22 | 2021-11-25 | Neuway Pharma Gmbh | Vlp for the treatment of leukodystrophies |
| CN113336655A (zh) * | 2020-12-30 | 2021-09-03 | 江西迪赛诺制药有限公司 | 一种(r)-3-氨基丁醇的制备方法 |
| CN116925022B (zh) * | 2023-07-06 | 2025-08-01 | 江苏信和生物医药有限公司 | 一种(s)-5-烯丙基-2-氧杂双环[3.3.0]辛-8-烯的制备方法 |
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| US7169744B2 (en) * | 2002-06-06 | 2007-01-30 | Procter & Gamble Company | Organic catalyst with enhanced solubility |
| WO2008062878A1 (fr) | 2006-11-22 | 2008-05-29 | Nihon Nohyaku Co., Ltd. | Nouveau dérivé de pyrazole, agent de lutte contre des organismes nuisibles et utilisation de l'agent de lutte contre des organismes nuisibles |
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| WO2010038200A1 (en) * | 2008-10-01 | 2010-04-08 | Actelion Pharmaceuticals Ltd | Oxazolidine compounds as orexin receptor antagonists |
| WO2010044054A1 (en) * | 2008-10-14 | 2010-04-22 | Actelion Pharmaceuticals Ltd | Phenethylamide derivatives and their heterocyclic analogues |
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