LT4005B - Substituted 4-phenyl-4-piperidinecarboxamides with both local anaesthetic and analgesic effect as well as processes for their preparation - Google Patents

Substituted 4-phenyl-4-piperidinecarboxamides with both local anaesthetic and analgesic effect as well as processes for their preparation Download PDF

Info

Publication number: LT4005B
Authority: LT; Lithuania
Prior art keywords: formula; compound; compounds; preparation; phenyl
Prior art date: 1989-12-21

Application number

LTIP1731A

Other languages

English (en)

Lithuanian (lt)

Inventor

Anna-Lena Ask

Rune Verner 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

1993-12-30

Publication date

1996-07-25

1993-12-30 Application filed by Astra Ab filed Critical Astra Ab

1995-07-25 Publication of LTIP1731A publication Critical patent/LTIP1731A/xx

1996-07-25 Publication of LT4005B publication Critical patent/LT4005B/lt

Links

238000002360 preparation method Methods 0.000 title claims abstract description 8
238000000034 method Methods 0.000 title claims abstract description 4
230000000202 analgesic effect Effects 0.000 title claims description 11
230000003444 anaesthetic effect Effects 0.000 title claims description 8
230000008569 process Effects 0.000 title claims 2
JPUKONSIEHCAQA-UHFFFAOYSA-N 4-phenylpiperidine-4-carboxamide Chemical class C=1C=CC=CC=1C1(C(=O)N)CCNCC1 JPUKONSIEHCAQA-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 49
239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 7
230000036592 analgesia Effects 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 6
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
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
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
206010002091 Anaesthesia Diseases 0.000 claims description 2
230000037005 anaesthesia Effects 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
241000272525 Anas platyrhynchos Species 0.000 claims 2
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 1
150000002148 esters Chemical class 0.000 claims 1
150000002825 nitriles Chemical class 0.000 claims 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 claims 1
238000002690 local anesthesia Methods 0.000 abstract description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000002904 solvent Substances 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 9
229960000482 pethidine Drugs 0.000 description 9
239000000243 solution Substances 0.000 description 9
239000000203 mixture Substances 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
239000003589 local anesthetic agent Substances 0.000 description 5
238000010992 reflux 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
239000011541 reaction mixture Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
229940035676 analgesics Drugs 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
239000003795 chemical substances by application Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000284 extract Substances 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
-1 pethidine compound Chemical class 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000002693 spinal anesthesia Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000012360 testing method Methods 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 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
DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 description 1
FOZVXADQAHVUSV-UHFFFAOYSA-N 1-bromo-2-(2-bromoethoxy)ethane Chemical compound BrCCOCCBr FOZVXADQAHVUSV-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
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
241001465754 Metazoa Species 0.000 description 1
208000004756 Respiratory Insufficiency Diseases 0.000 description 1
206010038678 Respiratory depression Diseases 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 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
229940035674 anesthetics Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229960003150 bupivacaine Drugs 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000000052 comparative effect Effects 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
238000013016 damping Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
206010013663 drug dependence Diseases 0.000 description 1
239000003480 eluent Substances 0.000 description 1
CYHIZAAGORDGHF-UHFFFAOYSA-N ethyl 1-(4-ethoxybutyl)-4-phenylpiperidine-4-carboxylate;hydrochloride Chemical compound Cl.C1CN(CCCCOCC)CCC1(C(=O)OCC)C1=CC=CC=C1 CYHIZAAGORDGHF-UHFFFAOYSA-N 0.000 description 1
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 1
WHQLQYRFIHPMNA-UHFFFAOYSA-N ethyl acetate;oxolane Chemical compound C1CCOC1.CCOC(C)=O WHQLQYRFIHPMNA-UHFFFAOYSA-N 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
238000009472 formulation Methods 0.000 description 1
238000007429 general method Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
230000003993 interaction 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
238000004519 manufacturing process Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 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
230000003533 narcotic effect Effects 0.000 description 1
QKHMFBKXTNQCTM-UHFFFAOYSA-N norpethidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCNCC1 QKHMFBKXTNQCTM-UHFFFAOYSA-N 0.000 description 1
230000036407 pain Effects 0.000 description 1
230000004526 pharmaceutical effect Effects 0.000 description 1
230000002980 postoperative effect Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000005556 structure-activity relationship Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
208000011117 substance-related disease Diseases 0.000 description 1
239000012085 test solution Substances 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)
General Health & Medical 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)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pain & Pain Management (AREA)
Public Health (AREA)
Rheumatology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (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)
Nitrogen Condensed Heterocyclic Rings (AREA)
Cosmetics (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

LTIP1731A 1989-12-21 1993-12-30 Substituted 4-phenyl-4-piperidinecarboxamides with both local anaesthetic and analgesic effect as well as processes for their preparation LT4005B (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
LTIP1731A LTIP1731A (en)	1995-07-25
LT4005B true LT4005B (en)	1996-07-25

Family

ID=20377821

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LTIP1731A LT4005B (en)	1989-12-21	1993-12-30	Substituted 4-phenyl-4-piperidinecarboxamides with both local anaesthetic and analgesic effect as well as processes for their preparation

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)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
TW548271B (en) *	1996-12-20	2003-08-21	Astra Pharma Inc	Novel piperidine derivatives having an exocyclic double bond with analgesic effects
SE9604786D0 (sv) *	1996-12-20	1996-12-20	Astra Pharma Inc	New compounds
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
CA2443672C (fr) *	2001-04-12	2011-03-29	Pharmacopeia, Inc.	Aryl et biaryl piperidines utilisees en tant qu'antagonistes de la mch
RU2203041C1 (ru) *	2001-12-27	2003-04-27	Закрытое акционерное общество "Брынцалов-А"	Спазмолитические таблетки бралангин
ATE496028T1 (de) *	2002-02-08	2011-02-15	Ono Pharmaceutical Co	Piperidinderivatverbindungen und arzneimittel, die diese verbindungen als wirkstoff enthalten
CN1744899A (zh) *	2002-12-13	2006-03-08	史密丝克莱恩比彻姆公司	作为ccr5拮抗剂的哌啶衍生物
US20100210633A1 (en) *	2006-10-12	2010-08-19	Epix Delaware, Inc.	Carboxamide compounds and their use
AU2008335135A1 (en)	2007-12-11	2009-06-18	Cytopathfinder, Inc.	Carboxamide compounds and their use as chemokine receptor agonists
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
EP3914246A1 (fr)	2019-01-22	2021-12-01	ICM (Institut du Cerveau et de la Moelle Épinière)	Anesthésique local pour le traitement de symptômes neurologiques résultant de dysfonctionnements cérébraux

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE96980C1 (fr)
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

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
CH498836A (de) *	1968-12-20	1970-11-15	Geigy Ag J R	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
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 UA UA5052485A patent/UA26403A/uk unknown
- 1990-12-17 WO PCT/SE1990/000818 patent/WO1991009845A1/fr not_active Ceased
- 1990-12-17 KR KR1019920701484A patent/KR0179382B1/ko not_active Expired - Fee Related
- 1990-12-17 JP JP3501896A patent/JP2656152B2/ja not_active Expired - Fee Related
- 1990-12-17 CA CA002069608A patent/CA2069608C/fr not_active Expired - Fee Related
- 1990-12-17 SG SG1996004491A patent/SG46413A1/en unknown
- 1990-12-17 EP EP91901571A patent/EP0506778B1/fr not_active Expired - Lifetime
- 1990-12-17 ES ES91901571T patent/ES2087280T3/es not_active Expired - Lifetime
- 1990-12-17 HU HU9202044A patent/HU213110B/hu unknown
- 1990-12-17 RO RO92-0832A patent/RO112864B1/ro unknown
- 1990-12-17 IE IE453490A patent/IE74855B1/en not_active IP Right Cessation
- 1990-12-17 IS IS3659A patent/IS1664B/is unknown
- 1990-12-17 AU AU69783/91A patent/AU647068B2/en not_active Ceased
- 1990-12-17 DK DK91901571.9T patent/DK0506778T3/da active
- 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
- 1990-12-20 EG EG74690A patent/EG19361A/xx active
- 1990-12-20 PT PT96303A patent/PT96303B/pt active IP Right Grant
- 1990-12-21 SK SK6581-90A patent/SK278283B6/sk unknown
- 1990-12-21 PL PL90288409A patent/PL163591B1/pl not_active IP Right Cessation
- 1990-12-21 CZ CS906581A patent/CZ278035B6/cs not_active IP Right Cessation
- 1990-12-21 US US07/633,246 patent/US5227389A/en not_active Expired - Lifetime
- 1990-12-21 CN CN90106009A patent/CN1037841C/zh not_active Expired - Fee Related
1991
- 1991-01-09 SA SA91110209A patent/SA91110209B1/ar unknown
1992
- 1992-06-17 NO NO922380A patent/NO178858C/no unknown
- 1992-06-17 FI FI922806A patent/FI100881B/fi not_active IP Right Cessation
- 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

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE96980C1 (fr)
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

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
D. G. HARDY, R. E. LISTER, E. S. STERN: "Structure-Activity Relationship of Some New Analogs of Pethidine", J. MED. CHEM., 1965, pages 847 - 851

Also Published As

Publication number	Publication date
DK0506778T3 (da)	1996-10-07
EG19361A (en)	1994-12-30
EP0506778B1 (fr)	1996-05-29
HU9202044D0 (en)	1992-09-28
LV10949A (lv)	1995-12-20
SK658190A3 (en)	1996-08-07
PT96303A (pt)	1991-09-30
HU213110B (en)	1997-02-28
SK278283B6 (en)	1996-08-07
LTIP1731A (en)	1995-07-25
KR927003531A (ko)	1992-12-18
FI922806L (fi)	1992-06-17
JPH05502869A (ja)	1993-05-20
SA91110209B1 (ar)	2004-05-08
IE74855B1 (en)	1997-08-13
IL96636A (en)	1994-11-28
NO922380D0 (no)	1992-06-17
YU234690A (sh)	1993-10-20
CZ278035B6 (en)	1993-07-14
CZ658190A3 (en)	1993-01-13
DE69027221T2 (de)	1996-10-10
UA26403A (uk)	1999-08-30
LV5766B4 (lv)	1997-06-20
YU48086B (sh)	1997-01-08
RU2039043C1 (ru)	1995-07-09
SI9012346A (sl)	1998-08-31
FI922806A0 (fi)	1992-06-17
HRP920591A2 (en)	1997-08-31
SI9012346B (sl)	1999-08-31
BG96513A (bg)	1993-12-24
AU647068B2 (en)	1994-03-17
ATE138650T1 (de)	1996-06-15
NZ236293A (en)	1992-10-28
BR1100379A (pt)	1999-12-07
WO1991009845A1 (fr)	1991-07-11
HRP920591B1 (en)	1998-12-31
BG60912B1 (bg)	1996-06-28
JP2656152B2 (ja)	1997-09-24
DZ1468A1 (fr)	2004-09-13
IS1664B (is)	1997-07-04
IL96636A0 (en)	1991-09-16
CA2069608C (fr)	2001-07-10
PL288409A1 (en)	1991-12-02
SG46413A1 (en)	1998-02-20
CN1053605A (zh)	1991-08-07
HK22997A (en)	1997-02-27
US5227389A (en)	1993-07-13
LV5766A4 (lv)	1996-12-20
CN1037841C (zh)	1998-03-25
CA2069608A1 (fr)	1991-06-22
PL163591B1 (pl)	1994-04-29
ES2087280T3 (es)	1996-07-16
PT96303B (pt)	1998-07-31
NO178858C (no)	1996-06-19
LV10949B (en)	1996-06-20
EP0506778A1 (fr)	1992-10-07
NO922380L (no)	1992-06-17
NO178858B (no)	1996-03-11
SE8904298D0 (sv)	1989-12-21
RO112864B1 (ro)	1998-01-30
FI100881B (fi)	1998-03-13
DE69027221D1 (de)	1996-07-04
IE904534A1 (en)	1991-07-03
IS3659A7 (is)	1991-06-22
KR0179382B1 (ko)	1999-03-20
AU6978391A (en)	1991-07-24
HUT64518A (en)	1994-01-28
US5360805A (en)	1994-11-01
ZA909903B (en)	1991-08-28

Legal Events

Date	Code	Title	Description
2006-08-25	MM9A	Lapsed patents	Effective date: 20051230

Publication	Publication Date	Title
US5360805A (en)	1994-11-01	Substituted 4-phenyl-4-piperidinecarboxamides with both local anaesthetic and analgesic effect as well as processes for their preparation
JP4035163B2 (ja)	2008-01-16	新規アリールグリシンアミド誘導体、その製造方法、及び該化合物を含有する医薬組成物
EP2044021B1 (fr)	2010-03-31	Procédé de préparation de rémifentanil, intermédiaires de celui-ci, utilisation desdits intermédiaires et procédés pour leur préparation
ES2858404T3 (es)	2021-09-30	Nuevos intermedios para la preparación de clorhidrato de remifentanilo
US6833457B1 (en)	2004-12-21	Process for preparation of benzylpiperidine compounds
US20060025444A1 (en)	2006-02-02	Fexofenadine base polymorphic forms
JP2002284763A (ja)	2002-10-03	ベンジルピペリジン化合物の製造方法