SE446335B - Ren enantiomer av en metasubstituerad 3-fenyl-1-propylpiperidin - Google Patents
Ren enantiomer av en metasubstituerad 3-fenyl-1-propylpiperidinInfo
- Publication number
- SE446335B SE446335B SE8202023A SE8202023A SE446335B SE 446335 B SE446335 B SE 446335B SE 8202023 A SE8202023 A SE 8202023A SE 8202023 A SE8202023 A SE 8202023A SE 446335 B SE446335 B SE 446335B
- Authority
- SE
- Sweden
- Prior art keywords
- group
- carbon atoms
- compound
- formula
- ppp
- Prior art date
Links
- BJGOULYFYANDMK-UHFFFAOYSA-N 3-phenyl-1-propylpiperidine Chemical class C1N(CCC)CCCC1C1=CC=CC=C1 BJGOULYFYANDMK-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 239000002253 acid Substances 0.000 claims abstract description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 abstract description 32
- -1 2,6-dimethylphenyl Chemical group 0.000 abstract description 13
- 238000002360 preparation method Methods 0.000 abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 8
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 abstract description 5
- 239000001257 hydrogen Substances 0.000 abstract description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 3
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
- 125000002252 acyl group Chemical group 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 2
- 150000002431 hydrogen Chemical class 0.000 abstract 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 208000035475 disorder Diseases 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
- 239000000203 mixture Substances 0.000 description 32
- 230000000694 effects Effects 0.000 description 25
- 241000700159 Rattus Species 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
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- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 18
- 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 description 17
- HTSNFXAICLXZMA-UHFFFAOYSA-N 3-(1-propyl-3-piperidinyl)phenol Chemical compound C1N(CCC)CCCC1C1=CC=CC(O)=C1 HTSNFXAICLXZMA-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 15
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 14
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- 230000001242 postsynaptic effect Effects 0.000 description 13
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 12
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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- 102000005962 receptors Human genes 0.000 description 11
- 108020003175 receptors Proteins 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 10
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- 238000001953 recrystallisation Methods 0.000 description 10
- 229960004046 apomorphine Drugs 0.000 description 9
- 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 9
- 238000001704 evaporation Methods 0.000 description 9
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- 229960003878 haloperidol Drugs 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 8
- OFKWWALNMPEOSZ-UHFFFAOYSA-N 3-(hydrazinylmethyl)phenol Chemical compound NNCC1=CC=CC(O)=C1 OFKWWALNMPEOSZ-UHFFFAOYSA-N 0.000 description 7
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 7
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- KTJLKTQSWVXPPM-UHFFFAOYSA-N 3-(3-methoxyphenyl)piperidine;hydrochloride Chemical compound Cl.COC1=CC=CC(C2CNCCC2)=C1 KTJLKTQSWVXPPM-UHFFFAOYSA-N 0.000 description 4
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- WADJLAVWIMPNPC-UHFFFAOYSA-N 2,3-dibenzoyloxy-2,3-dihydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)OC(O)(C(O)=O)C(O)(C(=O)O)OC(=O)C1=CC=CC=C1 WADJLAVWIMPNPC-UHFFFAOYSA-N 0.000 description 1
- PNBOVBWIGKATIC-UHFFFAOYSA-N 3-(1-propylpiperidin-3-yl)phenol;hydrobromide Chemical compound Br.C1N(CCC)CCCC1C1=CC=CC(O)=C1 PNBOVBWIGKATIC-UHFFFAOYSA-N 0.000 description 1
- VLGKCFSPDCPWPH-UHFFFAOYSA-N 3-(2-methoxyphenyl)-1-propylpiperidine;hydrochloride Chemical compound Cl.C1N(CCC)CCCC1C1=CC=CC=C1OC VLGKCFSPDCPWPH-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- YNLRDTBLEOQPQL-UHFFFAOYSA-N 3-piperidin-1-ylphenol Chemical compound OC1=CC=CC(N2CCCCC2)=C1 YNLRDTBLEOQPQL-UHFFFAOYSA-N 0.000 description 1
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- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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- 229920002472 Starch Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 206010043118 Tardive Dyskinesia Diseases 0.000 description 1
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
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- 239000004927 clay Substances 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 description 1
- 238000005661 deetherification reaction Methods 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940052760 dopamine agonists Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
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- 239000000975 dye Substances 0.000 description 1
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- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 235000021268 hot food Nutrition 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000003949 imides Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
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- AGJSNMGHAVDLRQ-HUUJSLGLSA-N methyl (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-HUUJSLGLSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- RSAFAYLZKCYUQW-UHFFFAOYSA-N n,n-di(propan-2-yl)carbamoyl chloride Chemical compound CC(C)N(C(C)C)C(Cl)=O RSAFAYLZKCYUQW-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001962 neuropharmacologic effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- BIFDXOOJPDHKJH-UHFFFAOYSA-N piperidine-1-carbonyl chloride Chemical compound ClC(=O)N1CCCCC1 BIFDXOOJPDHKJH-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000006289 propionylation Effects 0.000 description 1
- 238000010515 propionylation reaction Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003892 tartrate salts Chemical class 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
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
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Classifications
-
- 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
- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by 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
-
- 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
- A61P25/20—Hypnotics; Sedatives
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Public Health (AREA)
- Anesthesiology (AREA)
- Psychiatry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Saccharide Compounds (AREA)
- Cosmetics (AREA)
Priority Applications (21)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8202023A SE446335B (sv) | 1982-03-30 | 1982-03-30 | Ren enantiomer av en metasubstituerad 3-fenyl-1-propylpiperidin |
| NO831040A NO164024C (no) | 1982-03-30 | 1983-03-23 | Analogifremgangsmaate for fremstilling av terapeutisk aktive enantiomerer av substituerte fenylazacykloalkaner. |
| AU12845/83A AU564287B2 (en) | 1982-03-30 | 1983-03-25 | N-propyl,3-(substituted phenyl)piperidine |
| DE8383850084T DE3381885D1 (de) | 1982-03-30 | 1983-03-28 | Piperidinderivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate. |
| IE685/83A IE55261B1 (en) | 1982-03-30 | 1983-03-28 | Enantiomers of substituted phenylpiperidines |
| EP83850084A EP0097628B1 (en) | 1982-03-30 | 1983-03-28 | Piperidine derivatives, processes for their preparation and pharmaceutical preparation containing them |
| AT83850084T ATE56705T1 (de) | 1982-03-30 | 1983-03-28 | Piperidinderivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate. |
| CA000424804A CA1202307A (en) | 1982-03-30 | 1983-03-29 | (-)-3-(-hydroxyphenul)-n-n-propylpiperidine and derivatives thereof |
| ES521080A ES521080A0 (es) | 1982-03-30 | 1983-03-29 | Un procedimiento para preparar un enantiomero puro de un fenilazacicloalcano sustituido. |
| FI831068A FI81088C (fi) | 1982-03-30 | 1983-03-29 | Foerfarande foer framstaellning av farmakologiskt aktiva, rena enantiomerer av n-n-propyl-3-(3-hydroxifenyl)-piperidinderivater. |
| HU831073A HU191290B (en) | 1982-03-30 | 1983-03-29 | Process for preparing the enantiomers of substituted phenyl-piperidine derivatives |
| JP58051781A JPS58177971A (ja) | 1982-03-30 | 1983-03-29 | 置換フエニルアザシクロアルカン化合物およびド−パミンレセプタ−作働剤 |
| GR70924A GR79244B (en16) | 1982-03-30 | 1983-03-29 | |
| GB08308657A GB2117771B (en) | 1982-03-30 | 1983-03-29 | Enantiomers of substituted phenylazacycloalkanes |
| DK143483A DK162214C (da) | 1982-03-30 | 1983-03-29 | Analogifremgangsmaade til fremstilling af en ren enantiomer af 3-fenyl-n-n-propylpiperidinderivater |
| PT76481A PT76481B (en) | 1982-03-30 | 1983-03-30 | Process for preparing new enantiomers of substituted phenylazacycloalkanes and of pharmaceutical compositions |
| DD83249351A DD209621A5 (de) | 1982-03-30 | 1983-03-30 | Verfahren zur herstellung von enantiomeren substituierter phenylazacycloalkane |
| ES530186A ES530186A0 (es) | 1982-03-30 | 1984-03-01 | Un procedimiento para preparar un enantiomero puro de un fenilazacicloalcano sustituido |
| US06/656,616 US4719219A (en) | 1982-03-30 | 1984-10-01 | Phenyl-azacycloalkanes and use thereof in treatment of central nervous system disorders |
| ES539031A ES539031A0 (es) | 1982-03-30 | 1984-12-24 | Un procedimiento para preparar un enantiomero puro de un fenilazacicloalcano sustituido |
| US07/126,916 US4937346A (en) | 1979-12-05 | 1987-11-30 | Phenyl-azacykloalkanes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8202023A SE446335B (sv) | 1982-03-30 | 1982-03-30 | Ren enantiomer av en metasubstituerad 3-fenyl-1-propylpiperidin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8202023L SE8202023L (sv) | 1983-10-01 |
| SE446335B true SE446335B (sv) | 1986-09-01 |
Family
ID=20346417
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8202023A SE446335B (sv) | 1979-12-05 | 1982-03-30 | Ren enantiomer av en metasubstituerad 3-fenyl-1-propylpiperidin |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0097628B1 (en16) |
| JP (1) | JPS58177971A (en16) |
| AT (1) | ATE56705T1 (en16) |
| AU (1) | AU564287B2 (en16) |
| CA (1) | CA1202307A (en16) |
| DD (1) | DD209621A5 (en16) |
| DE (1) | DE3381885D1 (en16) |
| DK (1) | DK162214C (en16) |
| ES (3) | ES521080A0 (en16) |
| FI (1) | FI81088C (en16) |
| GB (1) | GB2117771B (en16) |
| GR (1) | GR79244B (en16) |
| HU (1) | HU191290B (en16) |
| IE (1) | IE55261B1 (en16) |
| NO (1) | NO164024C (en16) |
| PT (1) | PT76481B (en16) |
| SE (1) | SE446335B (en16) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8305362D0 (sv) * | 1983-09-30 | 1983-09-30 | Astra Laekemedel Ab | Novel substituted phenylazacycloalkanes, processes for preparation and pharmaceutical preparations for such compounds |
| SE9904724D0 (sv) * | 1999-12-22 | 1999-12-22 | Carlsson A Research Ab | New modulators of dopamine neurotransmission I |
| JP2011057619A (ja) * | 2009-09-10 | 2011-03-24 | Tokai Univ | 光学活性アミン化合物の製造方法、並びに、ジアステレオマー塩及びその製造方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU542153B2 (en) * | 1979-12-05 | 1985-02-07 | Per Arvid Emil Carlsson | New phenyl-azacycloalkanes |
-
1982
- 1982-03-30 SE SE8202023A patent/SE446335B/sv unknown
-
1983
- 1983-03-23 NO NO831040A patent/NO164024C/no unknown
- 1983-03-25 AU AU12845/83A patent/AU564287B2/en not_active Ceased
- 1983-03-28 IE IE685/83A patent/IE55261B1/en not_active IP Right Cessation
- 1983-03-28 EP EP83850084A patent/EP0097628B1/en not_active Expired - Lifetime
- 1983-03-28 AT AT83850084T patent/ATE56705T1/de not_active IP Right Cessation
- 1983-03-28 DE DE8383850084T patent/DE3381885D1/de not_active Expired - Fee Related
- 1983-03-29 GB GB08308657A patent/GB2117771B/en not_active Expired
- 1983-03-29 HU HU831073A patent/HU191290B/hu not_active IP Right Cessation
- 1983-03-29 CA CA000424804A patent/CA1202307A/en not_active Expired
- 1983-03-29 JP JP58051781A patent/JPS58177971A/ja active Granted
- 1983-03-29 GR GR70924A patent/GR79244B/el unknown
- 1983-03-29 FI FI831068A patent/FI81088C/fi not_active IP Right Cessation
- 1983-03-29 DK DK143483A patent/DK162214C/da not_active IP Right Cessation
- 1983-03-29 ES ES521080A patent/ES521080A0/es active Granted
- 1983-03-30 PT PT76481A patent/PT76481B/pt not_active IP Right Cessation
- 1983-03-30 DD DD83249351A patent/DD209621A5/de not_active IP Right Cessation
-
1984
- 1984-03-01 ES ES530186A patent/ES530186A0/es active Granted
- 1984-12-24 ES ES539031A patent/ES539031A0/es active Granted
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