SK658190A3 - Substituted piperidinecarboxamides, method of their manufacture, pharmaceutical drugs containing them and their application - Google Patents

Substituted piperidinecarboxamides, method of their manufacture, pharmaceutical drugs containing them and their application Download PDF

Info

Publication number: SK658190A3
Authority: SK; Slovakia
Prior art keywords: formula; substituted; piperidinecarboxamide; group; compounds
Prior art date: 1989-12-21

Application number

SK6581-90A

Other languages

English (en)

Slovak (sk)

Other versions

SK278283B6 (en

Inventor

Anna-Lena Ask

Rune V Sandberg

Original Assignee

Astra Ab

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.)

1989-12-21

Filing date

1990-12-21

Publication date

1996-08-07

1990-12-21 Application filed by Astra Ab filed Critical Astra Ab

1996-08-07 Publication of SK658190A3 publication Critical patent/SK658190A3/sk

1996-08-07 Publication of SK278283B6 publication Critical patent/SK278283B6/sk

Links

238000000034 method Methods 0.000 title claims abstract description 16
JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical class NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 title claims description 12
238000004519 manufacturing process Methods 0.000 title claims description 7
229940079593 drug Drugs 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 46
238000002360 preparation method Methods 0.000 claims abstract description 15
230000036592 analgesia Effects 0.000 claims abstract description 3
230000000202 analgesic effect Effects 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 9
230000003444 anaesthetic effect Effects 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 4
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
206010002091 Anaesthesia Diseases 0.000 claims 1
239000013543 active substance Substances 0.000 claims 1
230000037005 anaesthesia Effects 0.000 claims 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
150000002148 esters Chemical class 0.000 claims 1
238000007913 intrathecal administration Methods 0.000 claims 1
150000002825 nitriles Chemical class 0.000 claims 1
238000002690 local anesthesia Methods 0.000 abstract description 2
239000000825 pharmaceutical preparation Substances 0.000 abstract 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000000243 solution Substances 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
239000003589 local anesthetic agent Substances 0.000 description 7
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
238000003756 stirring Methods 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
-1 4-Ethoxybutyl Chemical group 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
PAMBGFPIHWBCRV-UHFFFAOYSA-N 1-hexyl-4-phenylpiperidine-4-carboxylic acid;hydrochloride Chemical compound Cl.C1CN(CCCCCC)CCC1(C(O)=O)C1=CC=CC=C1 PAMBGFPIHWBCRV-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000000730 antalgic agent Substances 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
HEWMAXKQJUUEFK-UHFFFAOYSA-N ethyl 1-hexyl-4-phenylpiperidine-4-carboxylate;hydrochloride Chemical compound Cl.C1CN(CCCCCC)CCC1(C(=O)OCC)C1=CC=CC=C1 HEWMAXKQJUUEFK-UHFFFAOYSA-N 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000003193 general anesthetic agent Substances 0.000 description 2
239000005457 ice water Substances 0.000 description 2
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
229960000482 pethidine Drugs 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000002693 spinal anesthesia Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
GVMVWWOZCINRMT-UHFFFAOYSA-N 1-(2-ethoxyethyl)-4-phenylpiperidine-4-carbonitrile Chemical compound C1CN(CCOCC)CCC1(C#N)C1=CC=CC=C1 GVMVWWOZCINRMT-UHFFFAOYSA-N 0.000 description 1
SJSSSWXOQBSRTP-UHFFFAOYSA-N 1-(2-ethoxyethyl)-4-phenylpiperidine-4-carboxylic acid;hydrochloride Chemical compound Cl.C1CN(CCOCC)CCC1(C(O)=O)C1=CC=CC=C1 SJSSSWXOQBSRTP-UHFFFAOYSA-N 0.000 description 1
GOKUDEWVRNZXDZ-UHFFFAOYSA-N 1-bromo-3-(3-bromopropoxy)propane Chemical compound BrCCCOCCCBr GOKUDEWVRNZXDZ-UHFFFAOYSA-N 0.000 description 1
ARWWHHYRUKOURQ-UHFFFAOYSA-N 1-butyl-4-phenylpiperidine-4-carboxamide Chemical class C1CN(CCCC)CCC1(C(N)=O)C1=CC=CC=C1 ARWWHHYRUKOURQ-UHFFFAOYSA-N 0.000 description 1
LEBVLXFERQHONN-UHFFFAOYSA-N 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide Chemical compound CCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C LEBVLXFERQHONN-UHFFFAOYSA-N 0.000 description 1
IXRDURXALZYREB-UHFFFAOYSA-N 1-chloro-4-ethoxybutane Chemical compound CCOCCCCCl IXRDURXALZYREB-UHFFFAOYSA-N 0.000 description 1
ANOOTOPTCJRUPK-UHFFFAOYSA-N 1-iodohexane Chemical compound CCCCCCI ANOOTOPTCJRUPK-UHFFFAOYSA-N 0.000 description 1
DMCVVFIWYIKAEJ-UHFFFAOYSA-N 4-phenylpiperidine-4-carbonitrile Chemical compound C=1C=CC=CC=1C1(C#N)CCNCC1 DMCVVFIWYIKAEJ-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
206010013654 Drug abuse Diseases 0.000 description 1
208000004550 Postoperative Pain Diseases 0.000 description 1
208000004756 Respiratory Insufficiency Diseases 0.000 description 1
206010038678 Respiratory depression Diseases 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229940035676 analgesics Drugs 0.000 description 1
229940035674 anesthetics Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
229960003150 bupivacaine Drugs 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
239000000284 extract Substances 0.000 description 1
JXJPYHDHJZJWRI-UHFFFAOYSA-N fenpiprane Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)CCN1CCCCC1 JXJPYHDHJZJWRI-UHFFFAOYSA-N 0.000 description 1
229960002428 fentanyl Drugs 0.000 description 1
IVLVTNPOHDFFCJ-UHFFFAOYSA-N fentanyl citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1N(C(=O)CC)C(CC1)CCN1CCC1=CC=CC=C1 IVLVTNPOHDFFCJ-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229960005015 local anesthetics Drugs 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical group [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 1
238000002483 medication Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
229960005181 morphine Drugs 0.000 description 1
ZJVHJWSKZOLGCZ-UHFFFAOYSA-N n-butyl-1-methyl-4-phenylpiperidine-4-carboxamide Chemical compound C=1C=CC=CC=1C1(C(=O)NCCCC)CCN(C)CC1 ZJVHJWSKZOLGCZ-UHFFFAOYSA-N 0.000 description 1
RZKLJVMZMYEYCM-UHFFFAOYSA-N n-ethyl-1-hexyl-4-phenylpiperidine-4-carboxamide Chemical compound C1CN(CCCCCC)CCC1(C(=O)NCC)C1=CC=CC=C1 RZKLJVMZMYEYCM-UHFFFAOYSA-N 0.000 description 1
239000002547 new drug Substances 0.000 description 1
239000000014 opioid analgesic Substances 0.000 description 1
229940005483 opioid analgesics Drugs 0.000 description 1
230000004526 pharmaceutical effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
208000011117 substance-related disease Diseases 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
- C07D211/64—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having an aryl radical as the second substituent in position 4
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Pain & Pain Management (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Bioinformatics & Cheminformatics (AREA)
Rheumatology (AREA)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)
Cosmetics (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

SK6581-90A 1989-12-21 1990-12-21 Substituted piperidinecarboxamides, method of their manufacture, pharmaceutical drugs containing them and their application SK278283B6 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
SE8904298A SE8904298D0 (sv)	1989-12-21	1989-12-21	New compounds

Publications (2)

Publication Number	Publication Date
SK658190A3 true SK658190A3 (en)	1996-08-07
SK278283B6 SK278283B6 (en)	1996-08-07

Family

ID=20377821

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK6581-90A SK278283B6 (en)	1989-12-21	1990-12-21	Substituted piperidinecarboxamides, method of their manufacture, pharmaceutical drugs containing them and their application

Country Status (40)

Country	Link
US (2)	US5227389A (fr)
EP (1)	EP0506778B1 (fr)
JP (1)	JP2656152B2 (fr)
KR (1)	KR0179382B1 (fr)
CN (1)	CN1037841C (fr)
AT (1)	ATE138650T1 (fr)
AU (1)	AU647068B2 (fr)
BG (1)	BG60912B1 (fr)
BR (1)	BR1100379A (fr)
CA (1)	CA2069608C (fr)
CZ (1)	CZ278035B6 (fr)
DE (1)	DE69027221T2 (fr)
DK (1)	DK0506778T3 (fr)
DZ (1)	DZ1468A1 (fr)
EG (1)	EG19361A (fr)
ES (1)	ES2087280T3 (fr)
FI (1)	FI100881B (fr)
HK (1)	HK22997A (fr)
HR (1)	HRP920591B1 (fr)
HU (1)	HU213110B (fr)
IE (1)	IE74855B1 (fr)
IL (1)	IL96636A (fr)
IS (1)	IS1664B (fr)
LT (1)	LT4005B (fr)
LV (2)	LV10949B (fr)
NO (1)	NO178858C (fr)
NZ (1)	NZ236293A (fr)
PL (1)	PL163591B1 (fr)
PT (1)	PT96303B (fr)
RO (1)	RO112864B1 (fr)
RU (1)	RU2039043C1 (fr)
SA (1)	SA91110209B1 (fr)
SE (1)	SE8904298D0 (fr)
SG (1)	SG46413A1 (fr)
SI (1)	SI9012346B (fr)
SK (1)	SK278283B6 (fr)
UA (1)	UA26403A (fr)
WO (1)	WO1991009845A1 (fr)
YU (1)	YU48086B (fr)
ZA (1)	ZA909903B (fr)

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JP3916092B2 (ja) *	1993-09-17	2007-05-16	杏林製薬株式会社	イミダゾリジノン誘導体とその酸付加塩及び老年性痴呆症の治療薬
SE9400447D0 (sv) *	1994-02-11	1994-02-11	Astra Ab	New compounds
SE9404438D0 (sv) *	1994-12-21	1994-12-21	Astra Ab	New process
US5931809A (en) *	1995-07-14	1999-08-03	Depotech Corporation	Epidural administration of therapeutic compounds with sustained rate of release
GB9600235D0 (en) *	1996-01-05	1996-03-06	Pfizer Ltd	Therapeutic agents
DE19642591A1 (de) *	1996-10-15	1998-04-16	Basf Ag	Neue Piperidin-Ketocarbonsäure-Derivate, deren Herstellung und Anwendung
SE9604786D0 (sv) *	1996-12-20	1996-12-20	Astra Pharma Inc	New compounds
TW548271B (en) *	1996-12-20	2003-08-21	Astra Pharma Inc	Novel piperidine derivatives having an exocyclic double bond with analgesic effects
RU2125878C1 (ru) *	1996-12-26	1999-02-10	Новокузнецкий научно-исследовательский химико-фармацевтический институт	Анальгетическое средство
RU2117481C1 (ru) *	1997-07-15	1998-08-20	Государственный научно-исследовательский институт органической химии и технологии	Анальгетическое средство и способ его приготовления
US7799337B2 (en)	1997-07-21	2010-09-21	Levin Bruce H	Method for directed intranasal administration of a composition
US20020102291A1 (en) *	1997-12-15	2002-08-01	Noven Pharmaceuticals, Inc.	Compositions and method for treatment of attention deficit disorder and attention deficit/hyperactivity disorder with methylphenidate
SE9803240D0 (sv) *	1998-09-24	1998-09-24	Diabact Ab	A pharmaceutical composition having a rapid action
SE9803239D0 (sv) *	1998-09-24	1998-09-24	Diabact Ab	Composition for the treatment of acute pain
ATE460163T1 (de) *	2001-04-12	2010-03-15	Pharmacopeia Llc	Arly und diaryl piperidinderivate verwendbar als mch-hemmer
RU2203041C1 (ru) *	2001-12-27	2003-04-27	Закрытое акционерное общество "Брынцалов-А"	Спазмолитические таблетки бралангин
DE60335788D1 (de) *	2002-02-08	2011-03-03	Ono Pharmaceutical Co	Piperidinderivatverbindungen und arzneimittel, die diese verbindungen als wirkstoff enthalten
RU2005118407A (ru) *	2002-12-13	2006-03-10	СмитКлайн Бичем Корпорейшн (US)	Производные пиперидина в качестве антагонистов ccr5
CL2007002958A1 (es) *	2006-10-12	2008-05-09	Epix Delaware Inc	Compuestos derivados de heteroaril-carboxamida, antagonistas del receptor de quimioquina; composicion farmaceutica; y uso para el tratamiento o prevencion de enfermedades tales como rechazo de transplante de organos, artritis reumatoidea, lupus, entr
KR20100102646A (ko)	2007-12-11	2010-09-24	가부시키가이샤 사이토파스파인더	카르복스아미드 화합물 및 케모카인 수용체 길항제로서의 이의 용도
US8473062B2 (en)	2008-05-01	2013-06-25	Autonomic Technologies, Inc.	Method and device for the treatment of headache
US8412336B2 (en)	2008-12-29	2013-04-02	Autonomic Technologies, Inc.	Integrated delivery and visualization tool for a neuromodulation system
US9320908B2 (en)	2009-01-15	2016-04-26	Autonomic Technologies, Inc.	Approval per use implanted neurostimulator
US8494641B2 (en)	2009-04-22	2013-07-23	Autonomic Technologies, Inc.	Implantable neurostimulator with integral hermetic electronic enclosure, circuit substrate, monolithic feed-through, lead assembly and anchoring mechanism
US20220096452A1 (en)	2019-01-22	2022-03-31	Icm (Institut Du Cerveau Et De La Moelle Épinière)	Local anesthetic for the treatment of neurological symptoms resulting from brain dysfunctions

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE96980C1 (fr)
US2486796A (en) *	1943-06-25	1949-11-01	Ciba Pharm Prod Inc	Esters of 1-alkyl-4-hydroxyphenylpiperidyl-4-ketones
US3334106A (en) *	1964-10-20	1967-08-01	Aldrich Chem Co Inc	N(aryl)n(hydrocarbyl)-omega-(4-phenyl-4-piperidinocarbonylheteroamine) alkanoamide
US3539580A (en) *	1967-06-26	1970-11-10	Janssen Pharm	4-aryl-4-aminoalkoxy-piperidines
CH501622A (de) *	1968-12-20	1971-01-15	Ciba Geigy Ag	Verfahren zur Herstellung von neuen Piperidinderivaten
US3737538A (en) *	1968-12-30	1973-06-05	Ciba Geigy Corp	Antitussive compositions and method with isonipecotic acid derivatives
FR2156470A2 (en) *	1971-10-21	1973-06-01	Synthelabo	1-(3,3-diphenyl-1-propyl)-4-aryl-piperidines - as analgesics spasmolytic and anti-tussive agents
ZA899436B (en) *	1988-12-12	1990-08-29	Ciba Geigy	Piperidine derivatives
US5100903A (en) *	1989-05-12	1992-03-31	Anaquest, Inc.	N-aryl-n-(1-substituted-3-alkoxy-4-piperidinyl)amides and pharmaceutical compositions and methods employing such compounds

1989
- 1989-12-21 SE SE8904298A patent/SE8904298D0/xx unknown
1990
- 1990-11-30 NZ NZ236293A patent/NZ236293A/xx unknown
- 1990-12-10 ZA ZA909903A patent/ZA909903B/xx unknown
- 1990-12-11 IL IL9663690A patent/IL96636A/en not_active IP Right Cessation
- 1990-12-12 SI SI9012346A patent/SI9012346B/sl not_active IP Right Cessation
- 1990-12-12 YU YU234690A patent/YU48086B/sh unknown
- 1990-12-12 DZ DZ900223A patent/DZ1468A1/fr active
- 1990-12-17 ES ES91901571T patent/ES2087280T3/es not_active Expired - Lifetime
- 1990-12-17 RO RO92-0832A patent/RO112864B1/ro unknown
- 1990-12-17 AU AU69783/91A patent/AU647068B2/en not_active Ceased
- 1990-12-17 CA CA002069608A patent/CA2069608C/fr not_active Expired - Fee Related
- 1990-12-17 WO PCT/SE1990/000818 patent/WO1991009845A1/fr not_active Ceased
- 1990-12-17 EP EP91901571A patent/EP0506778B1/fr not_active Expired - Lifetime
- 1990-12-17 SG SG1996004491A patent/SG46413A1/en unknown
- 1990-12-17 IE IE453490A patent/IE74855B1/en not_active IP Right Cessation
- 1990-12-17 DK DK91901571.9T patent/DK0506778T3/da active
- 1990-12-17 IS IS3659A patent/IS1664B/is unknown
- 1990-12-17 DE DE69027221T patent/DE69027221T2/de not_active Expired - Fee Related
- 1990-12-17 AT AT91901571T patent/ATE138650T1/de not_active IP Right Cessation
- 1990-12-17 HU HU9202044A patent/HU213110B/hu unknown
- 1990-12-17 JP JP3501896A patent/JP2656152B2/ja not_active Expired - Fee Related
- 1990-12-17 UA UA5052485A patent/UA26403A/uk unknown
- 1990-12-17 KR KR1019920701484A patent/KR0179382B1/ko not_active Expired - Fee Related
- 1990-12-20 PT PT96303A patent/PT96303B/pt active IP Right Grant
- 1990-12-20 EG EG74690A patent/EG19361A/xx active
- 1990-12-21 SK SK6581-90A patent/SK278283B6/sk unknown
- 1990-12-21 CN CN90106009A patent/CN1037841C/zh not_active Expired - Fee Related
- 1990-12-21 CZ CS906581A patent/CZ278035B6/cs not_active IP Right Cessation
- 1990-12-21 PL PL90288409A patent/PL163591B1/pl not_active IP Right Cessation
- 1990-12-21 US US07/633,246 patent/US5227389A/en not_active Expired - Lifetime
1991
- 1991-01-09 SA SA91110209A patent/SA91110209B1/ar unknown
1992
- 1992-06-17 FI FI922806A patent/FI100881B/fi not_active IP Right Cessation
- 1992-06-17 NO NO922380A patent/NO178858C/no unknown
- 1992-06-19 RU SU925052485A patent/RU2039043C1/ru not_active IP Right Cessation
- 1992-06-19 BG BG96513A patent/BG60912B1/bg unknown
- 1992-09-29 HR HRP-2346/90A patent/HRP920591B1/xx not_active IP Right Cessation
1993
- 1993-07-12 US US08/090,416 patent/US5360805A/en not_active Expired - Lifetime
- 1993-08-27 LV LVP-93-1042A patent/LV10949B/lv unknown
- 1993-12-30 LT LTIP1731A patent/LT4005B/lt not_active IP Right Cessation
1996
- 1996-07-17 LV LV960262A patent/LV5766B4/xx unknown
1997
- 1997-02-27 HK HK22997A patent/HK22997A/en not_active IP Right Cessation
- 1997-04-30 BR BR1100379-0A patent/BR1100379A/pt active IP Right Grant

Also Published As

Publication number	Publication date
NO178858C (no)	1996-06-19
BR1100379A (pt)	1999-12-07
IS3659A7 (is)	1991-06-22
CZ278035B6 (en)	1993-07-14
LV10949A (lv)	1995-12-20
YU234690A (sh)	1993-10-20
BG96513A (bg)	1993-12-24
EP0506778A1 (fr)	1992-10-07
LTIP1731A (en)	1995-07-25
NZ236293A (en)	1992-10-28
FI922806L (fi)	1992-06-17
US5360805A (en)	1994-11-01
ZA909903B (en)	1991-08-28
HRP920591B1 (en)	1998-12-31
PL163591B1 (pl)	1994-04-29
CZ658190A3 (en)	1993-01-13
SI9012346B (sl)	1999-08-31
HU9202044D0 (en)	1992-09-28
IL96636A0 (en)	1991-09-16
IE74855B1 (en)	1997-08-13
SK278283B6 (en)	1996-08-07
JP2656152B2 (ja)	1997-09-24
NO922380D0 (no)	1992-06-17
AU647068B2 (en)	1994-03-17
LT4005B (en)	1996-07-25
HUT64518A (en)	1994-01-28
WO1991009845A1 (fr)	1991-07-11
RU2039043C1 (ru)	1995-07-09
SI9012346A (sl)	1998-08-31
LV5766B4 (lv)	1997-06-20
HK22997A (en)	1997-02-27
IE904534A1 (en)	1991-07-03
LV10949B (en)	1996-06-20
YU48086B (sh)	1997-01-08
BG60912B1 (bg)	1996-06-28
CN1053605A (zh)	1991-08-07
HRP920591A2 (en)	1997-08-31
EG19361A (en)	1994-12-30
EP0506778B1 (fr)	1996-05-29
DE69027221D1 (de)	1996-07-04
NO178858B (no)	1996-03-11
DK0506778T3 (da)	1996-10-07
PL288409A1 (en)	1991-12-02
LV5766A4 (lv)	1996-12-20
FI922806A0 (fi)	1992-06-17
ATE138650T1 (de)	1996-06-15
SE8904298D0 (sv)	1989-12-21
ES2087280T3 (es)	1996-07-16
CA2069608C (fr)	2001-07-10
FI100881B (fi)	1998-03-13
PT96303B (pt)	1998-07-31
KR0179382B1 (ko)	1999-03-20
DE69027221T2 (de)	1996-10-10
IL96636A (en)	1994-11-28
PT96303A (pt)	1991-09-30
UA26403A (uk)	1999-08-30
CN1037841C (zh)	1998-03-25
HU213110B (en)	1997-02-28
JPH05502869A (ja)	1993-05-20
KR927003531A (ko)	1992-12-18
CA2069608A1 (fr)	1991-06-22
SA91110209B1 (ar)	2004-05-08
DZ1468A1 (fr)	2004-09-13
NO922380L (no)	1992-06-17
US5227389A (en)	1993-07-13
RO112864B1 (ro)	1998-01-30
AU6978391A (en)	1991-07-24
IS1664B (is)	1997-07-04
SG46413A1 (en)	1998-02-20

Publication	Publication Date	Title
RU2039043C1 (ru)	1995-07-09	Производное n-замещенного 1-гексил-4-фенил-4-пиперидинкарбоксамида или его фармацевтически приемлемая соль и способ его получения
CA2010011C (fr)	1997-12-02	N-phenyl-n-(4-piperidinyl) amides utiles comme analgesiques
US4289772A (en)	1981-09-15	1-Piperidinophthalazines as cardiac stimulants
NO153082B (no)	1985-10-07	Apparat for stapping av en rynket roerformet omhylling
US4542127A (en)	1985-09-17	Antidiabetic salicylic acid derivatives
SK281931B6 (sk)	2001-09-11	Deriváty piperidín-4-karboxamidu s analgetickými a lokálne anestetickými účinkami, spôsob ich prípravy, farmaceutický prípravok s ich obsahom a ich použitie
HK14086A (en)	1986-03-07	2-(4-(diphenylmethylene)-1-piperidinyl)-acetic acids and their amides, their preparation and pharmaceutical preparations containing them
EP0315405A1 (fr)	1989-05-10	Dérivés de la 4-phényle-4-(N-(2-fluorophényl)amido)pipéridine
WO1995033723A1 (fr)	1995-12-14	Piperidines, pyrrolidines, morpholines et thiomorpholines a substitution phenoxyalcoyle, en tant qu'antagonistes des canaux a calciques
US3325502A (en)	1967-06-13	1-allyl-3-(3-hydroxyphenyl)-piperidine compounds
NO881899L (no)	1988-11-03	Nye 2-aminoalkyl-4-benzyl-1-(2h)-ftalazino-derivater.
JP3190717B2 (ja)	2001-07-23	新規な置換イタコン酸誘導体
EP0763021A1 (fr)	1997-03-19	Piperidines, pyrrolidines, morpholines et tiopmorpholines a substitution phenoxyalcoyle en tant qu'antagonistes des canaux calciques
DE3882677T2 (de)	1993-11-04	Kardiovaskulaer aktive verbindungen.
JPH05230023A (ja)	1993-09-07	１，４−ジヒドロピリジン誘導体、その製法と用途
DD259189A5 (de)	1988-08-17	Verfahren zur herstellung neuer hydropyridin-derivate