DD153117A5 - Verfahren zur herstellung von n-phenoxyalkylpiperidin-derivaten - Google Patents

Verfahren zur herstellung von n-phenoxyalkylpiperidin-derivaten Download PDF

Info

Publication number: DD153117A5
Authority: DD; German Democratic Republic
Prior art keywords: group; propoxy; radical; piperidino; benzonitrile
Prior art date: 1979-09-28

Application number

DD80224197A

Other languages

German (de)

English (en)

Inventor

Walter-Gunar Friebe

Wolfgang Kampe

Max Thiel

Wolfgang Schaumann

Otto-Henning Wilhelms

Original Assignee

Boehringer Mannheim Gmbh

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1979-09-28

Filing date

1980-09-24

Publication date

1981-12-23

1980-09-24 Application filed by Boehringer Mannheim Gmbh filed Critical Boehringer Mannheim Gmbh

1981-12-23 Publication of DD153117A5 publication Critical patent/DD153117A5/de

Links

238000000034 method Methods 0.000 title claims description 15
238000002360 preparation method Methods 0.000 title claims description 13
230000008569 process Effects 0.000 title claims description 9
-1 acyl radical Chemical class 0.000 claims abstract description 56
150000001875 compounds Chemical class 0.000 claims abstract description 41
150000003839 salts Chemical class 0.000 claims abstract description 23
150000003254 radicals Chemical class 0.000 claims abstract description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims abstract description 6
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
125000003277 amino group Chemical group 0.000 claims abstract description 4
125000001841 imino group Chemical group [H]N=* 0.000 claims abstract description 3
125000003107 substituted aryl group Chemical group 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 2
KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 claims description 18
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 6
239000007795 chemical reaction product Substances 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
230000001387 anti-histamine Effects 0.000 abstract description 2
239000000739 antihistaminic agent Substances 0.000 abstract description 2
230000001741 anti-phlogistic effect Effects 0.000 abstract 1
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 52
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 51
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
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125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
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WRTQJBLGXMBDSD-UHFFFAOYSA-N [2-[[1-[3-(2-cyanophenoxy)propyl]piperidin-4-yl]carbamoyl]phenyl] acetate Chemical compound CC(=O)OC1=CC=CC=C1C(=O)NC1CCN(CCCOC=2C(=CC=CC=2)C#N)CC1 WRTQJBLGXMBDSD-UHFFFAOYSA-N 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000004913 activation Effects 0.000 description 1
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125000002723 alicyclic group Chemical group 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
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FQPFAHBPWDRTLU-UHFFFAOYSA-N aminophylline Chemical compound NCCN.O=C1N(C)C(=O)N(C)C2=C1NC=N2.O=C1N(C)C(=O)N(C)C2=C1NC=N2 FQPFAHBPWDRTLU-UHFFFAOYSA-N 0.000 description 1
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239000007864 aqueous solution Substances 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
230000004872 arterial blood pressure Effects 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
MXOQNVMDKHLYCZ-UHFFFAOYSA-N benzamidoxime Chemical compound ON=C(N)C1=CC=CC=C1 MXOQNVMDKHLYCZ-UHFFFAOYSA-N 0.000 description 1
LZCZIHQBSCVGRD-UHFFFAOYSA-N benzenecarboximidamide;hydron;chloride Chemical compound [Cl-].NC(=[NH2+])C1=CC=CC=C1 LZCZIHQBSCVGRD-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
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239000002775 capsule Substances 0.000 description 1
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125000001589 carboacyl group Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
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239000007979 citrate buffer Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000008139 complexing agent Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
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125000000753 cycloalkyl group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
HXCKCCRKGXHOBK-UHFFFAOYSA-N cycloheptane Chemical compound [CH]1CCCCCC1 HXCKCCRKGXHOBK-UHFFFAOYSA-N 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000012738 dissolution medium Substances 0.000 description 1
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239000003480 eluent Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
HUCSIQVACXREBW-UHFFFAOYSA-N ethyl 2-[2-[3-(4-benzamidopiperidin-1-yl)propoxy]phenyl]-6-oxo-1h-pyrimidine-5-carboxylate;hydrochloride Chemical compound Cl.N1C(=O)C(C(=O)OCC)=CN=C1C1=CC=CC=C1OCCCN1CCC(NC(=O)C=2C=CC=CC=2)CC1 HUCSIQVACXREBW-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000036541 health Effects 0.000 description 1
JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
210000004731 jugular vein Anatomy 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 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
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
125000005905 mesyloxy group Chemical group 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
PLTCINJSRCMVPL-UHFFFAOYSA-N n-(2h-tetrazol-5-yl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC=1N=NNN=1 PLTCINJSRCMVPL-UHFFFAOYSA-N 0.000 description 1
WWRZUCAXACNFSZ-UHFFFAOYSA-N n-[1-(3-chloropropyl)piperidin-4-yl]benzamide Chemical compound C1CN(CCCCl)CCC1NC(=O)C1=CC=CC=C1 WWRZUCAXACNFSZ-UHFFFAOYSA-N 0.000 description 1
FVLVBVSILSHUAF-UHFFFAOYSA-N n-benzyl-3,5-dimethyl-n-propan-2-ylbenzamide Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N(C(C)C)CC1=CC=CC=C1 FVLVBVSILSHUAF-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229940092253 ovalbumin Drugs 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229960002275 pentobarbital sodium Drugs 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
229940107700 pyruvic acid Drugs 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
239000011541 reaction mixture Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 1
229960000581 salicylamide Drugs 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
230000008313 sensitization Effects 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
FIGCISKOGMXHSJ-UHFFFAOYSA-N sodium diazide Chemical compound [N-]=[N+]=[N-].[Na]N=[N+]=[N-] FIGCISKOGMXHSJ-UHFFFAOYSA-N 0.000 description 1
WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
238000012360 testing method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
238000001665 trituration Methods 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1

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
- C07D211/36—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 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 to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Immunology (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Hydrogenated Pyridines (AREA)

DD80224197A 1979-09-28 1980-09-24 Verfahren zur herstellung von n-phenoxyalkylpiperidin-derivaten DD153117A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19792939292 DE2939292A1 (de)	1979-09-28	1979-09-28	N-phenoxyalkylpiperidin-derivate, verfahrenn zu deren herstellung sowie diese verbindungen enthaltende arzneimittel

Publications (1)

Publication Number	Publication Date
DD153117A5 true DD153117A5 (de)	1981-12-23

Family

ID=6082088

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD80224197A DD153117A5 (de)	1979-09-28	1980-09-24	Verfahren zur herstellung von n-phenoxyalkylpiperidin-derivaten

Country Status (10)

Country	Link
US (1)	US4348401A (cs)
EP (1)	EP0026876B1 (cs)
JP (1)	JPS5668669A (cs)
AT (1)	ATE2519T1 (cs)
CA (1)	CA1139759A (cs)
CS (1)	CS219950B2 (cs)
DD (1)	DD153117A5 (cs)
DE (2)	DE2939292A1 (cs)
ES (1)	ES495412A0 (cs)
IL (1)	IL61114A0 (cs)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1996006828A1 (en) *	1994-08-29	1996-03-07	Richter Gedeon Vegyészeti Gyár Rt.	Piperidinoalkyl aryl ethers and pharmaceutical compositions containing them

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* Cited by examiner, † Cited by third party
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DE3209271A1 (de) *	1982-03-13	1983-09-15	Boehringer Mannheim Gmbh, 6800 Mannheim	Bicyclische phenolether, verfahren zu deren herstellung sowie diese verbindungen enthaltende arzneimittel
FR2681319B1 (fr) *	1991-09-12	1995-02-17	Synthelabo	Derives de 1-(phenoxyalkyl)piperidine, leur preparation et leur application en therapeutique.
GB9319534D0 (en) *	1993-09-22	1993-11-10	Boots Co Plc	Therapeutic agents
ZA9610741B (en)	1995-12-22	1997-06-24	Warner Lambert Co	4-Substituted piperidine analogs and their use as subtype selective nmda receptor antagonists
ZA9610736B (en)	1995-12-22	1997-06-27	Warner Lambert Co	2-Substituted piperidine analogs and their use as subtypeselective nmda receptor antagonists
ZA9610738B (en)	1995-12-22	1997-06-24	Warner Lambert Co	Subtype selective nmda receptor ligands and the use thereof
ZA9610745B (en) *	1995-12-22	1997-06-24	Warner Lambert Co	4-Subsituted piperidine analogs and their use as subtype selective nmda receptor antagonists
EA007270B1 (ru) *	2002-03-13	2006-08-25	Янссен Фармацевтика Н.В.	Пиперазинил-, пиперидинил- и морфолинилпроизводные как новые ингибиторы гистондеацетилазы
CA2476067C (en) *	2002-03-13	2011-09-20	Janssen Pharmaceutica N.V.	Carbonylamino-derivatives as novel inhibitors of histone deacetylase
ES2306880T3 (es)	2002-03-13	2008-11-16	Janssen Pharmaceutica Nv	Derivados de sulfonilamino como inhibidores novedosos de la histona desacetilasa.
AU2003218737B2 (en)	2002-03-13	2008-04-10	Janssen Pharmaceutica N.V.	Inhibitors of histone deacetylase
PL1781639T3 (pl) *	2004-07-28	2012-07-31	Janssen Pharmaceutica Nv	Podstawione pochodne indolilo-alkiloaminowe jako nowe inhibitory deacetylazy histonowej
BRPI0607910A2 (pt) *	2005-04-07	2010-03-23	Toyama Chemical Co Ltd	composiÇço farmacÊutica para tratar infecÇÕes féngicas, e, mÉtodo de uso de um derivado de arilamidina ou um sal do mesmo
AU2006248938B2 (en)	2005-05-18	2011-09-29	Janssen Pharmaceutica N.V.	Substituted aminopropenyl piperidine or morpholine derivatives as novel inhibitors of histone deacetylase
CA2635015C (en) *	2006-01-19	2014-06-03	Janssen Pharmaceutica N.V.	Substituted indolyl-alkyl-amino-derivatives as inhibitors of histone deacetylase
JP5247470B2 (ja)	2006-01-19	2013-07-24	ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ	ヒストンデアセチラーゼのインヒビターとしてのピリジン及びピリミジン誘導体
US8101616B2 (en) *	2006-01-19	2012-01-24	Janssen Pharmaceutica N.V.	Pyridine and pyrimidine derivatives as inhibitors of histone deacetylase
DE602007001190D1 (de) *	2006-01-19	2009-07-09	Janssen Pharmaceutica Nv	Aminophenylderivate als neue inhibitoren von histondeacetylase
AU2007254179B2 (en)	2006-05-18	2013-03-21	Pharmacyclics Llc	Intracellular kinase inhibitors
KR102077864B1 (ko)	2012-08-01	2020-02-14	쇼와 덴코 패키징 가부시키가이샤	내용물 부착 방지 덮개재

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US3255196A (en) *		1966-06-07		Phenoxyalkyl piperidine derivatives
CH411880A (fr) *	1962-02-28	1966-04-30	Rhone Poulenc Sa	Procédé de préparation de nouveaux dérivés de la pipéridine
US3691176A (en) *	1970-05-25	1972-09-12	Abbott Lab	1-(4-fluorophenoxypropyl)-4-anilino-piperidines
DE2341376A1 (de) *	1972-08-24	1974-03-07	Ciba Geigy Ag	Piperidin-derivate und verfahren zu ihrer herstellung
GB1533383A (en) *	1974-11-15	1978-11-22	Science Union & Cie	Arylethers and heterocyclic ethers processes for their preparation and pharmaceutical compositions containing them
US4027028A (en) *	1975-11-10	1977-05-31	Science Union Et Cie	Arylethers and pharmaceutical compositions
DE2737630A1 (de) *	1977-08-20	1979-03-01	Boehringer Mannheim Gmbh	Neue aminopropanolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel

1979
- 1979-09-28 DE DE19792939292 patent/DE2939292A1/de not_active Withdrawn
1980
- 1980-09-10 US US06/185,839 patent/US4348401A/en not_active Expired - Lifetime
- 1980-09-23 IL IL61114A patent/IL61114A0/xx unknown
- 1980-09-24 EP EP80105725A patent/EP0026876B1/de not_active Expired
- 1980-09-24 DE DE8080105725T patent/DE3062052D1/de not_active Expired
- 1980-09-24 DD DD80224197A patent/DD153117A5/de unknown
- 1980-09-24 AT AT80105725T patent/ATE2519T1/de not_active IP Right Cessation
- 1980-09-26 JP JP13415080A patent/JPS5668669A/ja active Pending
- 1980-09-26 ES ES495412A patent/ES495412A0/es active Granted
- 1980-09-26 CA CA000361880A patent/CA1139759A/en not_active Expired
- 1980-09-29 CS CS806568A patent/CS219950B2/cs unknown

Cited By (1)

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Publication number	Priority date	Publication date	Assignee	Title
WO1996006828A1 (en) *	1994-08-29	1996-03-07	Richter Gedeon Vegyészeti Gyár Rt.	Piperidinoalkyl aryl ethers and pharmaceutical compositions containing them

Also Published As

Publication number	Publication date
EP0026876A1 (de)	1981-04-15
ES8105729A1 (es)	1981-06-16
JPS5668669A (en)	1981-06-09
ES495412A0 (es)	1981-06-16
CS219950B2 (en)	1983-03-25
IL61114A0 (en)	1980-11-30
ATE2519T1 (de)	1983-03-15
DE2939292A1 (de)	1981-04-09
CA1139759A (en)	1983-01-18
EP0026876B1 (de)	1983-02-16
US4348401A (en)	1982-09-07
DE3062052D1 (en)	1983-03-24

Publication	Publication Date	Title
EP0026876B1 (de)	1983-02-16	N-Phenoxyalkylpiperidin-Derivate, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel
EP0503162B1 (de)	1998-04-22	Azol-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung
DE2058295C3 (de)	1980-06-19	Xanthen-9-on-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE69032414T2 (de)	1998-11-19	Diphenylmethane derivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammenstellungen
DE3336024A1 (de)	1985-04-18	4-amino-l-benzyl-pyrrolidinone und ihre saeureadditionssalze, verfahren zu ihrer herstellung und arzneimittel
EP0013894B1 (de)	1982-02-03	Neue Arylether, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel
DE2065636A1 (de)	1974-12-19	Neue tricyclische verbindungen
WO1995001350A1 (en)	1995-01-12	Tetrazole derivatives having antihistaminic and antiallergic activity
DE68917220T2 (de)	1994-12-01	Phenylpyridon-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen.
DD154364A5 (de)	1982-03-17	Verfahren zur herstellung von neuen derivaten des piperidylbenzimidazolinons
EP1210335B1 (de)	2005-09-14	Aminocarbonyl-substituierte benzimidazolderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
EP0089028B1 (de)	1988-05-25	Neue Theophyllin-Derivate und Verfahren zu ihrer Herstellung
EP0171645B1 (de)	1988-11-30	Neue 2H-1-Benzopyran-2-on-Derivate, Verfahren zu ihrer Herstellung und Arzneimittel, die diese Verbindungen enthalten
DE2334009A1 (de)	1975-01-23	Purin-derivate sowie verfahren zu ihrer herstellung
DE2550000A1 (de)	1977-05-12	Neue purin-derivate und verfahren zu ihrer herstellung
DD219642A5 (de)	1985-03-13	Verfahren zur herstellung von bis-(piperazinyl- bzw. homopiperazinyl)alkanen
EP0064255A1 (de)	1982-11-10	Benzopyranylether, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel und Zwischenprodukte
EP0021103B1 (de)	1983-05-25	Theophyllin-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DD150001A5 (de)	1981-08-12	Verfahren zur herstellung einer pyranon-verbindung
DE69005904T2 (de)	1994-05-05	Phenylpyrimidonderivate.
DE3875030T2 (de)	1993-03-04	Leukotrien-antagonisten.
EP0003558A1 (de)	1979-08-22	9-(3-Piperidinopropyl)-purin-Derivate, Verfahren zu deren Herstellung, deren Verwendung sowie diese Verbindungen enthaltende Arzneimittel
DE2340217C2 (de)	1982-02-25	3-Benzoylthiophene, ihre Salze, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE4427056B4 (de)	2006-08-03	Neue Carboxymethylidencycloheptimidazol-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als antihypertensive und anticongestive Mittel
DE1929921A1 (de)	1970-01-02	Neue 1-Alyl-1,2,5,6-tetrahydro-3-pyridylmethyl-carbonsaeureester sowie deren Saeureadditionssalze und quaternaere Ammoniumverbindungen

DD153117A5 - Verfahren zur herstellung von n-phenoxyalkylpiperidin-derivaten - Google Patents

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