UA71590C2 - Piperazine and piperidine derivatives - Google Patents
Piperazine and piperidine derivatives Download PDFInfo
- Publication number
- UA71590C2 UA71590C2 UA2001064076A UA2001064076A UA71590C2 UA 71590 C2 UA71590 C2 UA 71590C2 UA 2001064076 A UA2001064076 A UA 2001064076A UA 2001064076 A UA2001064076 A UA 2001064076A UA 71590 C2 UA71590 C2 UA 71590C2
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- Prior art keywords
- formula
- compound
- hydrogen
- alkyl
- compounds
- Prior art date
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 150000003053 piperidines Chemical class 0.000 title claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 10
- 150000003839 salts Chemical group 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 239000000651 prodrug Chemical group 0.000 claims abstract 2
- 229940002612 prodrug Drugs 0.000 claims abstract 2
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- -1 amino- Chemical class 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical class O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 230000008484 agonism Effects 0.000 abstract description 8
- 230000000694 effects Effects 0.000 abstract description 8
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 abstract description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 abstract 1
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 abstract 1
- 102000004980 Dopamine D2 Receptors Human genes 0.000 abstract 1
- 108090001111 Dopamine D2 Receptors Proteins 0.000 abstract 1
- 230000001404 mediated effect Effects 0.000 abstract 1
- 229940076279 serotonin Drugs 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
- 102000005962 receptors Human genes 0.000 description 10
- 108020003175 receptors Proteins 0.000 description 10
- 241000700159 Rattus Species 0.000 description 8
- 229960003638 dopamine Drugs 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 4
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 230000001143 conditioned effect Effects 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000006399 behavior Effects 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 239000011265 semifinished product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 208000019901 Anxiety disease Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 102000030621 adenylate cyclase Human genes 0.000 description 2
- 108060000200 adenylate cyclase Proteins 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 2
- 229960004046 apomorphine Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000000506 psychotropic effect Effects 0.000 description 2
- 230000002787 reinforcement Effects 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PHGAOXNFCZKFTR-UHFFFAOYSA-N 3-methylpiperidin-2-one Chemical compound CC1CCCNC1=O PHGAOXNFCZKFTR-UHFFFAOYSA-N 0.000 description 1
- AVCVKLFYUIZIDL-UHFFFAOYSA-N 4-(1-ethyl-3,6-dihydro-2h-pyridin-4-yl)-1,3-dihydroindol-2-one Chemical compound C1N(CC)CCC(C=2C=3CC(=O)NC=3C=CC=2)=C1 AVCVKLFYUIZIDL-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010003805 Autism Diseases 0.000 description 1
- 208000020706 Autistic disease Diseases 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 102000015554 Dopamine receptor Human genes 0.000 description 1
- 108050004812 Dopamine receptor Proteins 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- USQJWKLONNUHEV-UHFFFAOYSA-N N1CCNCC1.O1COC2=C1C=CC=C2.O2C=CC1=C2C=CC=C1 Chemical class N1CCNCC1.O1COC2=C1C=CC=C2.O2C=CC1=C2C=CC=C1 USQJWKLONNUHEV-UHFFFAOYSA-N 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 229940123445 Tricyclic antidepressant Drugs 0.000 description 1
- IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000164 antipsychotic agent Substances 0.000 description 1
- 229940005529 antipsychotics Drugs 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 210000004978 chinese hamster ovary cell Anatomy 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001054 cortical effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940095074 cyclic amp Drugs 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000009699 differential effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 230000003291 dopaminomimetic effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000013504 emergency use authorization Methods 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 238000012048 forced swim test Methods 0.000 description 1
- 208000037870 generalized anxiety Diseases 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 230000009191 jumping Effects 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 230000006742 locomotor activity Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000004031 partial agonist Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000003518 presynaptic effect Effects 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 230000000862 serotonergic effect Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/26—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98203871 | 1998-11-13 | ||
| PCT/EP1999/008702 WO2000029397A1 (en) | 1998-11-13 | 1999-11-10 | New piperazine and piperidine compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA71590C2 true UA71590C2 (en) | 2004-12-15 |
Family
ID=8234340
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2001064076A UA71590C2 (en) | 1998-11-13 | 1999-10-11 | Piperazine and piperidine derivatives |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US6780864B1 (cs) |
| EP (1) | EP1131308B1 (cs) |
| JP (1) | JP3638874B2 (cs) |
| KR (1) | KR100619465B1 (cs) |
| CN (1) | CN1225462C (cs) |
| AR (1) | AR021256A1 (cs) |
| AT (1) | ATE267183T1 (cs) |
| AU (1) | AU756470B2 (cs) |
| BR (1) | BR9915293B1 (cs) |
| CA (1) | CA2350137C (cs) |
| CZ (1) | CZ299774B6 (cs) |
| DE (1) | DE69917478T2 (cs) |
| DK (1) | DK1131308T3 (cs) |
| DZ (1) | DZ2934A1 (cs) |
| ES (1) | ES2217833T3 (cs) |
| HU (1) | HUP0104922A3 (cs) |
| IL (2) | IL143028A0 (cs) |
| MX (1) | MXPA01004854A (cs) |
| NO (1) | NO318888B1 (cs) |
| NZ (1) | NZ511584A (cs) |
| PL (1) | PL193685B1 (cs) |
| RU (1) | RU2225406C2 (cs) |
| SI (1) | SI1131308T1 (cs) |
| SK (1) | SK285648B6 (cs) |
| TW (1) | TWI252230B (cs) |
| UA (1) | UA71590C2 (cs) |
| WO (1) | WO2000029397A1 (cs) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| AU2001267421A1 (en) * | 2000-05-12 | 2001-11-20 | Solvay Pharmaceuticals B.V. | Use of compounds having combined dopamine d2, 5-ht1a and alpha adrenoreceptor agonistic action for treating cns disorders |
| AU6392701A (en) * | 2000-05-12 | 2001-11-20 | Solvay Pharm Bv | Piperazine and piperidine compounds |
| MXPA03004249A (es) * | 2000-11-14 | 2003-09-22 | Merck Patent Gmbh | Nuevos usos de combinaciones selectivas antagonistas del receptor de dopamina d2 y agonistas del receptor de 5-ht1a. |
| AR034206A1 (es) * | 2001-02-16 | 2004-02-04 | Solvay Pharm Bv | Un procedimiento para la preparacion de mesilatos de derivados de piperazina y dichos mesilatos |
| US6800648B2 (en) | 2001-04-26 | 2004-10-05 | Wyeth | Antipsychotic aminomethyl derivatives of 7,8-dihydro-3H-1,6,9-trioxa-3-AZA-cyclopenta[a]naphthalen-2-one |
| US6743796B2 (en) | 2001-05-07 | 2004-06-01 | Wyeth | Piperazinyl-isatins |
| AU2002322539B2 (en) | 2001-07-20 | 2007-09-27 | Psychogenics Inc. | Treatment for attention-deficit hyperactivity disorder |
| EP1408964B1 (en) | 2001-07-26 | 2007-01-24 | MERCK PATENT GmbH | Use of 2- 5-(4-fluorophenyl)-3-pyridylmethylaminomethyl|-chromane and its physiologically acceptable salts |
| EP1336406A1 (en) * | 2002-02-14 | 2003-08-20 | Solvay Pharmaceuticals B.V. | Partial dopamine-D2 receptor agonist plus serotonin and/or noradrenaline inhibitory activity |
| WO2004000837A1 (ja) * | 2002-06-25 | 2003-12-31 | Sumitomo Pharmaceuticals Co., Ltd. | 新規なベンズオキサゾリノン誘導体 |
| US7435738B2 (en) | 2003-08-18 | 2008-10-14 | Solvay Pharmaceuticals, Inc. | Stable crystalline form of bifeprunox mesylate (7-[4-([1,1′-biphenyl]-3-ylmethyl)-1-piperazinyl]-2(3H)-benzoxazolone monomethanesulfonate) |
| EP1595542A1 (en) * | 2004-03-26 | 2005-11-16 | Solvay Pharmaceuticals B.V. | Transdermal iontophoretic delivery of piperazinyl-2(3H)-benzoxazolone compounds |
| US7596407B2 (en) | 2004-03-26 | 2009-09-29 | Solvay Pharmaceuticals, B.V. | Transdermal iontophoretic delivery of piperazinyl-2(3H)-benzoxazolone compounds |
| AU2005250103A1 (en) | 2004-05-27 | 2005-12-15 | Ucb | Benzoxazolone derivatives, processes for preparing them and their uses |
| US7405216B2 (en) | 2004-08-18 | 2008-07-29 | Solvay Pharmaceuticals, B.V. | Stable crystalline form of bifeprunox mesylate (7-[4-([1,1′-biphenyl]-3-ylmethyl)-1-piperazinyl]-2(3H)-benzoxazolone monomethanesulfonate) |
| US7423040B2 (en) | 2005-02-18 | 2008-09-09 | Irene Eijgendaal | Stable crystalline form of bifeprunox mesylate, dosage forms thereof and methods for using same |
| US7964604B2 (en) | 2005-02-18 | 2011-06-21 | Solvay Pharmaceuticals B.V. | Bifeprunox mesylate maintenance dose compositions and methods for using the same |
| PT1919883E (pt) * | 2005-08-22 | 2009-03-26 | Solvay Pharm Bv | N-óxidos como pró-medicamentos de derivados de piperazina & piperidina |
| US7750013B2 (en) | 2005-08-22 | 2010-07-06 | Solvay Pharmaceuticals, B.V. | N-oxides as prodrugs of piperazine and piperidine derivatives |
| AR058022A1 (es) * | 2005-08-22 | 2008-01-23 | Solvay Pharm Bv | Derivados de benzooxazoles, composiciones farmaceuticas y su uso para el tratamiento de desordenes del sistema nervioso. |
| US7786126B2 (en) | 2006-06-16 | 2010-08-31 | Solvay Pharmaceuticals B.V. | Combination preparations comprising SLV308 and a dopamine agonist |
| US8106056B2 (en) | 2006-06-16 | 2012-01-31 | Solvay Pharmaceuticals B.V. | Combination preparations comprising bifeprunox and a dopamine agonist |
| UY32935A (es) * | 2009-10-12 | 2011-05-31 | Abbott Healthcare Products Bv | Polimorfos de pardoprunox |
| JP7096813B2 (ja) | 2016-08-26 | 2022-07-06 | エクシーバ ゲーエムベーハー | 組成物及びその方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2567884B1 (fr) | 1984-07-19 | 1987-03-06 | Roussel Uclaf | Nouveaux derives de l'indole, leur preparation, leur application comme medicaments et les compositions les renfermant |
| ATE44528T1 (de) * | 1984-12-21 | 1989-07-15 | Duphar Int Res | Arzneimittel mit antipsychotischer wirkung. |
| ATE81975T1 (de) * | 1984-12-21 | 1992-11-15 | Duphar Int Res | Arzneimittel mit psychotroper wirkung. |
| DK148392D0 (da) | 1992-12-09 | 1992-12-09 | Lundbeck & Co As H | Heterocykliske forbindelser |
| ZA954689B (en) | 1994-06-08 | 1996-01-29 | Lundbeck & Co As H | 4-Aryl-1-(indanmethyl dihydrobenzofuranmethyl or dihydrobenzothiophenemethyl) piperidines tetrahydropyridines or piperazines |
| EP0773942A1 (en) | 1994-07-26 | 1997-05-21 | Pfizer Inc. | 4-indole derivatives as serotonin agonists and antagonists |
| ATE340173T1 (de) * | 1996-03-29 | 2006-10-15 | Duphar Int Res | Piperazin- und piperidin- derivate |
| EP0900792B1 (en) | 1997-09-02 | 2003-10-29 | Duphar International Research B.V | Piperazine and piperidine derivatives as 5-HT1A and dopamine D2-receptor (ant)agonists |
-
1999
- 1999-10-11 UA UA2001064076A patent/UA71590C2/uk unknown
- 1999-11-10 MX MXPA01004854A patent/MXPA01004854A/es not_active IP Right Cessation
- 1999-11-10 ES ES99955980T patent/ES2217833T3/es not_active Expired - Lifetime
- 1999-11-10 US US09/831,149 patent/US6780864B1/en not_active Expired - Fee Related
- 1999-11-10 SK SK649-2001A patent/SK285648B6/sk not_active IP Right Cessation
- 1999-11-10 DZ DZ990234A patent/DZ2934A1/xx active
- 1999-11-10 AU AU12709/00A patent/AU756470B2/en not_active Ceased
- 1999-11-10 PL PL99347635A patent/PL193685B1/pl not_active IP Right Cessation
- 1999-11-10 KR KR1020017005978A patent/KR100619465B1/ko not_active Expired - Fee Related
- 1999-11-10 DK DK99955980T patent/DK1131308T3/da active
- 1999-11-10 AT AT99955980T patent/ATE267183T1/de active
- 1999-11-10 CA CA002350137A patent/CA2350137C/en not_active Expired - Fee Related
- 1999-11-10 EP EP99955980A patent/EP1131308B1/en not_active Expired - Lifetime
- 1999-11-10 RU RU2001116117/04A patent/RU2225406C2/ru not_active IP Right Cessation
- 1999-11-10 JP JP2000582384A patent/JP3638874B2/ja not_active Expired - Fee Related
- 1999-11-10 DE DE69917478T patent/DE69917478T2/de not_active Expired - Lifetime
- 1999-11-10 CZ CZ20011657A patent/CZ299774B6/cs not_active IP Right Cessation
- 1999-11-10 NZ NZ511584A patent/NZ511584A/xx not_active IP Right Cessation
- 1999-11-10 SI SI9930574T patent/SI1131308T1/xx unknown
- 1999-11-10 IL IL14302899A patent/IL143028A0/xx active IP Right Grant
- 1999-11-10 HU HU0104922A patent/HUP0104922A3/hu unknown
- 1999-11-10 BR BRPI9915293-2A patent/BR9915293B1/pt not_active IP Right Cessation
- 1999-11-10 CN CNB998130710A patent/CN1225462C/zh not_active Expired - Fee Related
- 1999-11-10 WO PCT/EP1999/008702 patent/WO2000029397A1/en active IP Right Grant
- 1999-11-12 AR ARP990105763A patent/AR021256A1/es active IP Right Grant
-
2000
- 2000-01-05 TW TW089100097A patent/TWI252230B/zh not_active IP Right Cessation
-
2001
- 2001-05-08 IL IL143028A patent/IL143028A/en not_active IP Right Cessation
- 2001-05-11 NO NO20012339A patent/NO318888B1/no not_active IP Right Cessation
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