NO314185B1 - Nye alkoksyarylforbindelser, fremgangsmåte ved deres fremstilling og farmasöytiske sammensetninger inneholdende dem - Google Patents
Nye alkoksyarylforbindelser, fremgangsmåte ved deres fremstilling og farmasöytiske sammensetninger inneholdende dem Download PDFInfo
- Publication number
- NO314185B1 NO314185B1 NO19962210A NO962210A NO314185B1 NO 314185 B1 NO314185 B1 NO 314185B1 NO 19962210 A NO19962210 A NO 19962210A NO 962210 A NO962210 A NO 962210A NO 314185 B1 NO314185 B1 NO 314185B1
- Authority
- NO
- Norway
- Prior art keywords
- piperazine
- formula
- compound
- dihydro
- methoxybenzofuran
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 125000004171 alkoxy aryl group Chemical group 0.000 title 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 89
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 20
- 150000001408 amides Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
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- 208000035475 disorder Diseases 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 239000003446 ligand Substances 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- DLENTHUENMTSMJ-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-(1,2,3,4-tetrahydronaphthalen-2-ylmethyl)piperazine Chemical group O1CCOC2=CC(N3CCN(CC3)CC3CC4=CC=CC=C4CC3)=CC=C21 DLENTHUENMTSMJ-UHFFFAOYSA-N 0.000 claims description 2
- CYPJMEGEBKHODC-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-(2,3-dihydro-1h-inden-2-ylmethyl)piperazine Chemical group O1CCOC2=CC(N3CCN(CC3)CC3CC4=CC=CC=C4C3)=CC=C21 CYPJMEGEBKHODC-UHFFFAOYSA-N 0.000 claims description 2
- MEFQGPPTUONQCS-UHFFFAOYSA-N 1-(2,3-dihydro-1-benzofuran-5-yl)-4-(2,3-dihydro-1h-inden-2-ylmethyl)piperazine Chemical group C1=C2OCCC2=CC(N2CCN(CC2)CC2CC3=CC=CC=C3C2)=C1 MEFQGPPTUONQCS-UHFFFAOYSA-N 0.000 claims description 2
- DVZLGNMJPTZBFJ-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-2-ylmethyl)-4-(5-methoxy-2,3-dihydro-1-benzofuran-6-yl)piperazine Chemical group C1C2=CC=CC=C2CC1CN(CC1)CCN1C1=CC(OCC2)=C2C=C1OC DVZLGNMJPTZBFJ-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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 claims description 2
- 125000005905 mesyloxy group Chemical group 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
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- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract description 4
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- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
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- 239000000047 product Substances 0.000 description 52
- 239000000155 melt Substances 0.000 description 34
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- 230000000694 effects Effects 0.000 description 26
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- 238000012360 testing method Methods 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 23
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- 239000000243 solution Substances 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 19
- 241001465754 Metazoa Species 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 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 241000699666 Mus <mouse, genus> Species 0.000 description 17
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- 108020003175 receptors Proteins 0.000 description 15
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- 238000010992 reflux Methods 0.000 description 13
- QLVZLYLIPGRAQC-UHFFFAOYSA-N 1-(5-methoxy-2,3-dihydro-1-benzofuran-6-yl)piperazine Chemical compound COC1=CC=2CCOC=2C=C1N1CCNCC1 QLVZLYLIPGRAQC-UHFFFAOYSA-N 0.000 description 12
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- 241000699670 Mus sp. Species 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
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- 235000019341 magnesium sulphate Nutrition 0.000 description 9
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- FBKOLJGPLNOPEN-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-6-yl)piperazine Chemical class C1CNCCN1C1=CC=C(OCCO2)C2=C1 FBKOLJGPLNOPEN-UHFFFAOYSA-N 0.000 description 6
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- LZJOOZDHDBXADI-UHFFFAOYSA-N 1-(2h-1,5-benzodioxepin-7-yl)piperazine Chemical compound C1CNCCN1C1=CC=C(OCC=CO2)C2=C1 LZJOOZDHDBXADI-UHFFFAOYSA-N 0.000 description 2
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- 238000000835 electrochemical detection Methods 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 208000031424 hyperprolactinemia Diseases 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 108010024941 iodothyronine deiodinase type II Proteins 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 238000005567 liquid scintillation counting Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 150000002681 magnesium compounds Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229960002523 mercuric chloride Drugs 0.000 description 1
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
- IOQWAOZFIOUSPY-UHFFFAOYSA-N methyl 3-oxo-3-thiophen-3-ylpropanoate Chemical compound COC(=O)CC(=O)C=1C=CSC=1 IOQWAOZFIOUSPY-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 230000002474 noradrenergic effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000001817 pituitary effect Effects 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000952 serotonin receptor agonist Substances 0.000 description 1
- 230000002295 serotoninergic effect Effects 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- HRQDCDQDOPSGBR-UHFFFAOYSA-M sodium;octane-1-sulfonate Chemical compound [Na+].CCCCCCCCS([O-])(=O)=O HRQDCDQDOPSGBR-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 229960004940 sulpiride Drugs 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
- C07D321/02—Seven-membered rings
- C07D321/10—Seven-membered rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9506436A FR2734819B1 (fr) | 1995-05-31 | 1995-05-31 | Nouveaux composes de la piperazine, de la piperidine et de la 1,2,5,6-tetrahydropyridine, leur procede de preparation et les compositions pharmaceutiques les contenant |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO962210D0 NO962210D0 (no) | 1996-05-30 |
| NO962210L NO962210L (no) | 1996-12-02 |
| NO314185B1 true NO314185B1 (no) | 2003-02-10 |
Family
ID=9479526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19962210A NO314185B1 (no) | 1995-05-31 | 1996-05-30 | Nye alkoksyarylforbindelser, fremgangsmåte ved deres fremstilling og farmasöytiske sammensetninger inneholdende dem |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US5753662A (de) |
| EP (1) | EP0745598B1 (de) |
| JP (1) | JPH08325257A (de) |
| CN (1) | CN1064356C (de) |
| AT (1) | ATE204574T1 (de) |
| AU (1) | AU705374B2 (de) |
| CA (1) | CA2177774C (de) |
| DE (1) | DE69614608T2 (de) |
| DK (1) | DK0745598T3 (de) |
| ES (1) | ES2162989T3 (de) |
| FR (1) | FR2734819B1 (de) |
| GR (1) | GR3037040T3 (de) |
| NO (1) | NO314185B1 (de) |
| NZ (1) | NZ286698A (de) |
| PT (1) | PT745598E (de) |
| ZA (1) | ZA964485B (de) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19637237A1 (de) | 1996-09-13 | 1998-03-19 | Merck Patent Gmbh | Piperazin-Derivate |
| US6436940B2 (en) | 1996-12-20 | 2002-08-20 | H. Lundbeck A/S | Indane or dihydroindole derivatives |
| ES2205267T3 (es) * | 1996-12-20 | 2004-05-01 | H. Lundbeck A/S | Derivados de indano o de dihidroindol. |
| WO1998031679A1 (en) * | 1997-01-21 | 1998-07-23 | Yoshitomi Pharmaceutical Industries, Ltd. | Thiophene compounds and medicinal use thereof |
| FR2760014B1 (fr) * | 1997-02-27 | 1999-04-09 | Adir | Nouveaux composes de 2-amino indane, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2761358B1 (fr) * | 1997-03-27 | 1999-05-07 | Adir | Nouveaux composes de n-aryl piperidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2763589B1 (fr) * | 1997-05-22 | 2001-01-05 | Centre Nat Rech Scient | Composes pour la preparation de medicaments destines au traitement de pathologies impliquant le glutamate extracellulaire, et leurs procedes d'obtention |
| FR2769312B1 (fr) * | 1997-10-03 | 1999-12-03 | Adir | Nouveaux composes de l'indanol, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| CN1191248C (zh) * | 1997-10-24 | 2005-03-02 | 纽罗根公司 | 作为多巴胺d 受体亚型配体的1－(2－萘基)和1－(2－氮杂萘基)－4－(1－苯基甲基)哌嗪 |
| US6040448A (en) | 1997-10-24 | 2000-03-21 | Neurogen Corporation | Certain 1-(2-naphthyl) and 1-(2-azanaphthyl)-4-(1-phenylmethyl) piperazines, dopamine receptor subtype specific ligands |
| US6281216B1 (en) | 1998-02-09 | 2001-08-28 | Duphar International Research B.V. | 2-aminoquinoline derivatives having d4-agonistic activity |
| CA2324268A1 (en) * | 1998-03-18 | 1999-09-23 | Taisho Pharmaceutical Co., Ltd. | Aromaheterocyclic derivatives |
| CN1166665C (zh) | 1998-03-19 | 2004-09-15 | 日本农药株式会社 | 芳基哌啶衍生物及其用途 |
| EP0953567A3 (de) | 1998-04-29 | 2003-04-02 | Pfizer Products Inc. | Bizyklisch substituierte Piperazin-, Piperidin- und Tetrahydropyridin Derivate, deren Herstellung und deren Verwendung als Mittel mit zentraler dopaminerger (Dopamin D4 Rezeptor) Aktivität |
| WO1999064425A1 (en) * | 1998-06-09 | 1999-12-16 | Neurogen Corporation | Substituted thienocycloalkylpyrazoles: dopamine receptor subtype specific ligands |
| US6177566B1 (en) * | 1998-06-30 | 2001-01-23 | Neurogen Corporation | 6-(4-arylalkylpiperazin-1-yl) benzodioxane and 6-(4-arylalkylpiperazin-1-yl) chromane derivatives: dopamine receptor subtype specific ligands |
| US6806275B2 (en) | 2000-09-13 | 2004-10-19 | Nihon Nohyaku Co., Ltd. | Arylpiperidine derivatives and use thereof |
| EP2067775B1 (de) | 2001-07-16 | 2012-04-25 | Genzyme Corporation | N-Acylsphingosinglucosyltransferase-Inhibitor |
| FR2831166B1 (fr) * | 2001-10-18 | 2004-02-27 | Sanofi Synthelabo | Aralkyl-tetrahydro-pyridines, leur preparation et compositions pharmaceutiques les contenant |
| US7105513B2 (en) * | 2002-08-07 | 2006-09-12 | Sanofi-Avertis Deutschland Gmbh | Acylated, heteroaryl-condensed cycloalkenylamines and their use as pharmaceuticals |
| US6960611B2 (en) | 2002-09-16 | 2005-11-01 | Institute Of Materia Medica | Sulfonyl-containing 2,3-diarylindole compounds, methods for making same, and methods of use thereof |
| FR2884251B1 (fr) * | 2005-04-08 | 2007-07-13 | Servier Lab | Derives de piperazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| KR101431845B1 (ko) * | 2006-04-06 | 2014-08-25 | 바스프 에스이 | 개선된 색상 품질을 갖는 ｎ-알킬락탐의 제조 방법 |
| RU2011125705A (ru) * | 2008-11-24 | 2012-12-27 | Басф Се | Способ получения n-алкиллактама, обладающего улучшенным качеством цвета |
| EP2373617B1 (de) | 2008-12-04 | 2015-02-25 | Basf Se | Mischungen aus itaconsäure oder itaconsäurederivaten und primären aminen zur herstellung von 1,3- und 1,4-alkylmethylpyrrolidonen |
| WO2010084089A1 (en) | 2009-01-22 | 2010-07-29 | Basf Se | Mixtures of pvdf, n-alkyllactams and organic carbonate and their applications |
| US8369001B2 (en) * | 2009-07-17 | 2013-02-05 | The United States Of America, As Represented By The Secretary Of The Navy | Compact high power terahertz radiation cell |
| CA3140959A1 (en) | 2009-11-27 | 2011-06-03 | Genzyme Corporation | An amorphous and a crystalline form of genz 112638 hemitartrate as inhibitor of glucosylceramide synthase |
| SG10201510665WA (en) | 2009-12-04 | 2016-01-28 | Sunovion Pharmaceuticals Inc | Multicycle Compounds And Pharmaceutical Compositions Useful For The Treatment Of Neurological Disorders |
| PT3494119T (pt) | 2016-07-29 | 2024-12-10 | Pgi Drug Discovery Llc | Compostos e composições e seus usos |
| MA45795A (fr) | 2016-07-29 | 2019-06-05 | Sunovion Pharmaceuticals Inc | Composés et compositions, et utilisations associées |
| MX390141B (es) | 2017-02-16 | 2025-03-20 | Sunovion Pharmaceuticals Inc | Metodos para tratar esquizofrenia |
| CA3070993C (en) | 2017-08-02 | 2025-05-20 | Sunovion Pharmaceuticals Inc. | ISOCHROMANE COMPOUNDS AND THEIR USES |
| UA130249C2 (uk) | 2018-02-16 | 2025-12-31 | Сумітомо Фарма Америка, Інк. | Солі, кристалічні форми і способи їх отримання |
| EP3938045A1 (de) | 2019-03-14 | 2022-01-19 | Sunovion Pharmaceuticals Inc. | Salze einer isochromanylverbindung und kristalline formen, verfahren zur herstellung, therapeutische verwendungen und pharmazeutische zusammensetzungen davon |
| CA3180115A1 (en) | 2020-04-14 | 2021-10-21 | Sunovion Pharmaceuticals Inc. | (s)-(4,5-dihydro-7h-thieno[2,3-c]pyran-7-yl)-n-methylmethanamine for treating neurological and psychiatric disorders |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3377347A (en) * | 1963-06-14 | 1968-04-09 | Ciba Geigy Corp | Cyclobutene derivatives |
| DE2037852C3 (de) * | 1970-07-30 | 1980-06-26 | Boehringer Sohn Ingelheim | Neue Piperazinderivate und Verfahren zu ihrer Herstellung |
| US3859438A (en) * | 1971-07-08 | 1975-01-07 | Boehringer Sohn Ingelheim | Pharmaceutical compositions containing an n-(1-bicyclic aryl-propyl-2)-n-bicyclic aryl-piperazine and method of use |
| DE4017211A1 (de) * | 1990-05-29 | 1991-12-05 | Merck Patent Gmbh | Oxazolidinone |
| FR2670491B1 (fr) * | 1990-12-14 | 1993-02-05 | Adir | Nouvelles piperazines 1,4-disubstituees, leur procede de preparation et les compositions pharmaceutiques les renfermant. |
| DE4127849A1 (de) * | 1991-08-22 | 1993-02-25 | Merck Patent Gmbh | Benzodioxanderivate |
| FR2692264B1 (fr) * | 1992-06-12 | 1994-08-05 | Adir | Nouvelles piperazines 1,4-disubstituees, leur procede de preparation et les compositions pharmaceutiques les contenant. |
| DE4321366A1 (de) * | 1993-06-26 | 1995-01-05 | Merck Patent Gmbh | Piperidine und Piperazine |
-
1995
- 1995-05-31 FR FR9506436A patent/FR2734819B1/fr not_active Expired - Fee Related
-
1996
- 1996-05-29 JP JP8135195A patent/JPH08325257A/ja active Pending
- 1996-05-29 AU AU54558/96A patent/AU705374B2/en not_active Ceased
- 1996-05-30 NO NO19962210A patent/NO314185B1/no unknown
- 1996-05-30 CA CA002177774A patent/CA2177774C/fr not_active Expired - Fee Related
- 1996-05-30 US US08/655,457 patent/US5753662A/en not_active Expired - Fee Related
- 1996-05-30 CN CN96107770A patent/CN1064356C/zh not_active Expired - Fee Related
- 1996-05-30 ES ES96401156T patent/ES2162989T3/es not_active Expired - Lifetime
- 1996-05-30 DK DK96401156T patent/DK0745598T3/da active
- 1996-05-30 PT PT96401156T patent/PT745598E/pt unknown
- 1996-05-30 NZ NZ286698A patent/NZ286698A/en unknown
- 1996-05-30 EP EP96401156A patent/EP0745598B1/de not_active Expired - Lifetime
- 1996-05-30 AT AT96401156T patent/ATE204574T1/de not_active IP Right Cessation
- 1996-05-30 DE DE69614608T patent/DE69614608T2/de not_active Expired - Fee Related
- 1996-05-31 ZA ZA964485A patent/ZA964485B/xx unknown
-
1997
- 1997-01-30 US US08/792,179 patent/US5684020A/en not_active Expired - Fee Related
-
2001
- 2001-10-30 GR GR20010401912T patent/GR3037040T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPH08325257A (ja) | 1996-12-10 |
| US5684020A (en) | 1997-11-04 |
| FR2734819B1 (fr) | 1997-07-04 |
| AU5455896A (en) | 1996-12-12 |
| DE69614608T2 (de) | 2002-07-04 |
| EP0745598A1 (de) | 1996-12-04 |
| NO962210L (no) | 1996-12-02 |
| DE69614608D1 (de) | 2001-09-27 |
| NO962210D0 (no) | 1996-05-30 |
| DK0745598T3 (da) | 2001-10-08 |
| CN1064356C (zh) | 2001-04-11 |
| ES2162989T3 (es) | 2002-01-16 |
| US5753662A (en) | 1998-05-19 |
| AU705374B2 (en) | 1999-05-20 |
| FR2734819A1 (fr) | 1996-12-06 |
| CA2177774A1 (fr) | 1996-12-01 |
| PT745598E (pt) | 2001-11-30 |
| CA2177774C (fr) | 2001-07-24 |
| GR3037040T3 (en) | 2002-01-31 |
| ATE204574T1 (de) | 2001-09-15 |
| NZ286698A (en) | 1998-02-26 |
| EP0745598B1 (de) | 2001-08-22 |
| ZA964485B (en) | 1996-12-12 |
| CN1142494A (zh) | 1997-02-12 |
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