NO780040L - Fremgangsmaate ved fremstilling av nye piperidinderivater - Google Patents
Fremgangsmaate ved fremstilling av nye piperidinderivaterInfo
- Publication number
- NO780040L NO780040L NO780040A NO780040A NO780040L NO 780040 L NO780040 L NO 780040L NO 780040 A NO780040 A NO 780040A NO 780040 A NO780040 A NO 780040A NO 780040 L NO780040 L NO 780040L
- Authority
- NO
- Norway
- Prior art keywords
- piperidine
- diphenylmethylene
- hydroxybenzyl
- formula
- compound according
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 13
- 238000002360 preparation method Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 57
- -1 benzyl compound Chemical class 0.000 claims description 11
- 230000007062 hydrolysis Effects 0.000 claims description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims description 9
- UNPKOFGAQOEDMF-UHFFFAOYSA-N 4-benzhydrylidenepiperidine Chemical compound C1CNCCC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 UNPKOFGAQOEDMF-UHFFFAOYSA-N 0.000 claims description 6
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- UEMOJQPFXRHPNP-UHFFFAOYSA-N 4-[(4-benzhydrylidenepiperidin-1-yl)methyl]phenol Chemical group C1(=CC=CC=C1)C(=C1CCN(CC1)CC1=CC=C(C=C1)O)C1=CC=CC=C1 UEMOJQPFXRHPNP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- MRHLFZXYRABVOZ-UHFFFAOYSA-N diphenyl(pyridin-4-yl)methanol Chemical compound C=1C=CC=CC=1C(C=1C=CN=CC=1)(O)C1=CC=CC=C1 MRHLFZXYRABVOZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004970 halomethyl group Chemical group 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- MDTNCWGJXTWVEX-UHFFFAOYSA-N 4-benzhydrylidene-1-(piperidin-1-ylmethyl)cyclohexa-2,5-dien-1-ol Chemical compound C1(=CC=CC=C1)C(=C1C=CC(CN2CCCCC2)(C=C1)O)C1=CC=CC=C1 MDTNCWGJXTWVEX-UHFFFAOYSA-N 0.000 claims 4
- MTYPZYPJOJRYCY-UHFFFAOYSA-N 4-benzhydrylidene-1-benzylpiperidine Chemical compound C=1C=CC=CC=1CN(CC1)CCC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 MTYPZYPJOJRYCY-UHFFFAOYSA-N 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000155 melt Substances 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- 239000003179 convulsant agent Substances 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
- 150000003053 piperidines Chemical class 0.000 description 3
- 229910003446 platinum oxide Inorganic materials 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 206010010904 Convulsion Diseases 0.000 description 2
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 230000001773 anti-convulsant effect Effects 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 229960003965 antiepileptics Drugs 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000017531 blood circulation Effects 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 230000002490 cerebral effect Effects 0.000 description 2
- 230000036461 convulsion Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229960004815 meprobamate Drugs 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 1
- MISKQLXUTVKJLQ-UHFFFAOYSA-N 2-[(4-benzhydrylidenepiperidin-1-yl)methyl]phenol Chemical compound C1(=CC=CC=C1)C(=C1CCN(CC1)CC1=C(C=CC=C1)O)C1=CC=CC=C1 MISKQLXUTVKJLQ-UHFFFAOYSA-N 0.000 description 1
- QPJRIAVAXNAMCO-UHFFFAOYSA-N 3-[(4-benzhydrylidenepiperidin-1-yl)methyl]phenol Chemical compound C1(=CC=CC=C1)C(=C1CCN(CC1)CC1=CC(=CC=C1)O)C1=CC=CC=C1 QPJRIAVAXNAMCO-UHFFFAOYSA-N 0.000 description 1
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LLHTYIYHONUPTG-UHFFFAOYSA-N Cl.C1(=CC=CC=C1)C(=C1CCN(CC1)CC1=C(C=CC=C1)O)C1=CC=CC=C1 Chemical compound Cl.C1(=CC=CC=C1)C(=C1CCN(CC1)CC1=C(C=CC=C1)O)C1=CC=CC=C1 LLHTYIYHONUPTG-UHFFFAOYSA-N 0.000 description 1
- XQUZAKYXJUZAPU-UHFFFAOYSA-N Cl.C1(=CC=CC=C1)C(=C1CCN(CC1)CC1=CC=C(C=C1)O)C1=CC=CC=C1 Chemical compound Cl.C1(=CC=CC=C1)C(=C1CCN(CC1)CC1=CC=C(C=C1)O)C1=CC=CC=C1 XQUZAKYXJUZAPU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 206010043994 Tonic convulsion Diseases 0.000 description 1
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 1
- LQTUYTSNOWRKPB-UHFFFAOYSA-N [4-(bromomethyl)phenyl] benzoate Chemical compound C1=CC(CBr)=CC=C1OC(=O)C1=CC=CC=C1 LQTUYTSNOWRKPB-UHFFFAOYSA-N 0.000 description 1
- VCCQYMHQYVNIDC-UHFFFAOYSA-N [bromo(phenyl)methyl] benzoate Chemical class C=1C=CC=CC=1C(Br)OC(=O)C1=CC=CC=C1 VCCQYMHQYVNIDC-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000003556 anti-epileptic effect Effects 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- BWXZFPRLNQFEFD-UHFFFAOYSA-N bis(4-chlorophenyl)-piperidin-4-ylmethanol Chemical compound C=1C=C(Cl)C=CC=1C(C=1C=CC(Cl)=CC=1)(O)C1CCNCC1 BWXZFPRLNQFEFD-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125844 compound 46 Drugs 0.000 description 1
- 229940127271 compound 49 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- ZMISODWVFHHWNR-UHFFFAOYSA-N diphenyl(4-piperidinyl)methanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1CCNCC1 ZMISODWVFHHWNR-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000004 hemodynamic effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229960001789 papaverine Drugs 0.000 description 1
- 230000003836 peripheral circulation Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012439 solid excipient Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 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 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB931/77A GB1542823A (en) | 1977-01-11 | 1977-01-11 | Piperidine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO780040L true NO780040L (no) | 1978-07-12 |
Family
ID=9713045
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO780040A NO780040L (no) | 1977-01-11 | 1978-01-05 | Fremgangsmaate ved fremstilling av nye piperidinderivater |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS5387367A (sv) |
| BE (1) | BE862769A (sv) |
| BG (1) | BG28574A3 (sv) |
| CA (1) | CA1101426A (sv) |
| CS (1) | CS195652B2 (sv) |
| DD (1) | DD134089A5 (sv) |
| DE (1) | DE2800919A1 (sv) |
| DK (1) | DK5778A (sv) |
| ES (1) | ES465861A1 (sv) |
| FI (1) | FI780028A (sv) |
| FR (1) | FR2376846A1 (sv) |
| GB (1) | GB1542823A (sv) |
| IL (1) | IL53766A0 (sv) |
| IT (1) | IT1103117B (sv) |
| LU (1) | LU78839A1 (sv) |
| NL (1) | NL7800146A (sv) |
| NO (1) | NO780040L (sv) |
| PL (1) | PL203912A1 (sv) |
| PT (1) | PT67511B (sv) |
| SE (1) | SE7800184L (sv) |
| SU (2) | SU772482A3 (sv) |
| ZA (1) | ZA78158B (sv) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4650874A (en) * | 1984-11-26 | 1987-03-17 | G. D. Searle & Co. | N-(aralkoxybenzyl)-4(benzhydryl) piperidines |
| US4628095A (en) * | 1985-06-05 | 1986-12-09 | G. D. Searle & Co. | Substituted N-benzyl-4-(benzhydryl) piperidines |
| EP0228893A3 (en) * | 1985-12-20 | 1990-01-03 | A.H. ROBINS COMPANY, INCORPORATED (a Delaware corporation) | Arylalkyl-heterocyclic amines, n-substituted by aryloxyalkyl group in allergy treatment |
| GB9000305D0 (en) * | 1990-01-06 | 1990-03-07 | Pfizer Ltd | Anticholinergic agents |
| DE19681115D2 (de) * | 1995-12-20 | 1999-11-25 | Eckhart Pein | Neue 1-Phenylalkyl/Alkylen-4-(.Alpha.-Hydroxydiphenylmethyl)-Piperidin Derivative und ihre Verwendung als Serotonin Antagonisten |
| ATE292116T1 (de) * | 1998-01-16 | 2005-04-15 | Eisai Co Ltd | Verfahren zur herstellung von donepezilderivaten |
| BR0316747A (pt) * | 2002-12-18 | 2005-10-18 | Fmc Corp | Piperidinas n-(arilmetil substituìdas)-4-(metil dissubstituìdas) e piperazinas |
| EP1626044A4 (en) * | 2003-05-20 | 2008-08-20 | Ajinomoto Kk | NEW PIPERIDINE DERIVATIVE |
-
1977
- 1977-01-11 GB GB931/77A patent/GB1542823A/en not_active Expired
-
1978
- 1978-01-05 NO NO780040A patent/NO780040L/no unknown
- 1978-01-05 FI FI780028A patent/FI780028A/fi not_active Application Discontinuation
- 1978-01-05 NL NL7800146A patent/NL7800146A/xx not_active Application Discontinuation
- 1978-01-05 DK DK5778A patent/DK5778A/da unknown
- 1978-01-09 CS CS78170A patent/CS195652B2/cs unknown
- 1978-01-09 IL IL53766A patent/IL53766A0/xx unknown
- 1978-01-09 FR FR7800616A patent/FR2376846A1/fr active Granted
- 1978-01-09 BG BG7838343A patent/BG28574A3/xx unknown
- 1978-01-09 SE SE7800184A patent/SE7800184L/sv unknown
- 1978-01-10 PT PT67511A patent/PT67511B/pt unknown
- 1978-01-10 SU SU782562702A patent/SU772482A3/ru active
- 1978-01-10 JP JP147578A patent/JPS5387367A/ja active Granted
- 1978-01-10 LU LU78839A patent/LU78839A1/xx unknown
- 1978-01-10 IT IT47573/78A patent/IT1103117B/it active
- 1978-01-10 ES ES465861A patent/ES465861A1/es not_active Expired
- 1978-01-10 BE BE1008634A patent/BE862769A/xx not_active IP Right Cessation
- 1978-01-10 ZA ZA00780158A patent/ZA78158B/xx unknown
- 1978-01-10 DD DD78203161A patent/DD134089A5/xx unknown
- 1978-01-10 PL PL20391278A patent/PL203912A1/xx unknown
- 1978-01-10 DE DE19782800919 patent/DE2800919A1/de not_active Withdrawn
- 1978-01-10 CA CA294,674A patent/CA1101426A/en not_active Expired
- 1978-07-17 SU SU782637199A patent/SU990761A1/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| DK5778A (da) | 1978-07-12 |
| PT67511A (fr) | 1978-02-01 |
| FI780028A (fi) | 1978-07-12 |
| SU772482A3 (ru) | 1980-10-15 |
| BE862769A (fr) | 1978-07-10 |
| NL7800146A (nl) | 1978-07-13 |
| JPS6125031B2 (sv) | 1986-06-13 |
| CS195652B2 (en) | 1980-02-29 |
| DE2800919A1 (de) | 1978-07-13 |
| LU78839A1 (fr) | 1978-09-18 |
| FR2376846A1 (fr) | 1978-08-04 |
| SE7800184L (sv) | 1978-07-12 |
| JPS5387367A (en) | 1978-08-01 |
| PT67511B (fr) | 1979-06-11 |
| ES465861A1 (es) | 1978-09-16 |
| BG28574A3 (en) | 1980-05-15 |
| IT7847573A0 (it) | 1978-01-10 |
| IL53766A0 (en) | 1978-04-30 |
| ZA78158B (en) | 1978-10-25 |
| CA1101426A (en) | 1981-05-19 |
| SU990761A1 (ru) | 1983-01-23 |
| IT1103117B (it) | 1985-10-14 |
| FR2376846B1 (sv) | 1983-02-04 |
| GB1542823A (en) | 1979-03-28 |
| DD134089A5 (de) | 1979-02-07 |
| PL203912A1 (pl) | 1979-06-04 |
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