BG60912B1 - Заместени 4-фенил-4-пиперидинкарбоксамиди с локален обезболя- ващ и болкоуспокояващ ефект и метод за получаването им - Google Patents

Заместени 4-фенил-4-пиперидинкарбоксамиди с локален обезболя- ващ и болкоуспокояващ ефект и метод за получаването им Download PDF

Info

Publication number: BG60912B1
Authority: BG; Bulgaria
Prior art keywords: compound; formula; compounds; phenyl; preparation
Prior art date: 1989-12-21

Application number

BG96513A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG96513A (bg

Inventor

Anna-Lena Ask

Rune 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

1992-06-19

Publication date

1996-06-28

1992-06-19 Application filed by Astra Ab filed Critical Astra Ab

1993-12-24 Publication of BG96513A publication Critical patent/BG96513A/bg

1996-06-28 Publication of BG60912B1 publication Critical patent/BG60912B1/bg

Links

230000000202 analgesic effect Effects 0.000 title claims description 20
238000002360 preparation method Methods 0.000 title claims description 7
238000000034 method Methods 0.000 title abstract description 4
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
230000003119 painkilling effect Effects 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 45
239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 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
239000002253 acid Substances 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
208000002193 Pain Diseases 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
206010002091 Anaesthesia Diseases 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
230000037005 anaesthesia Effects 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims 1
239000012467 final product Substances 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
238000007913 intrathecal administration Methods 0.000 claims 1
150000002825 nitriles Chemical class 0.000 claims 1
230000036407 pain Effects 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
230000000699 topical effect Effects 0.000 abstract description 4
229940035676 analgesics Drugs 0.000 abstract description 3
239000000730 antalgic agent Substances 0.000 abstract description 3
229940124641 pain reliever Drugs 0.000 abstract 1
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
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
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 10
239000000243 solution Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
229960000482 pethidine Drugs 0.000 description 9
239000002904 solvent Substances 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
230000000694 effects Effects 0.000 description 5
239000000047 product Substances 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
238000003756 stirring Methods 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
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
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 3
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
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 2
125000004494 ethyl ester group Chemical group 0.000 description 2
239000000706 filtrate 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
230000035484 reaction time Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000002693 spinal anesthesia Methods 0.000 description 2
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
MMYKTRPLXXWLBC-UHFFFAOYSA-N 1-bromo-2-ethoxyethane Chemical compound CCOCCBr MMYKTRPLXXWLBC-UHFFFAOYSA-N 0.000 description 1
AZSSSYFLDBQDBQ-UHFFFAOYSA-N 1-butyl-4-phenylpiperidine-4-carboxylic acid Chemical compound C1CN(CCCC)CCC1(C(O)=O)C1=CC=CC=C1 AZSSSYFLDBQDBQ-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
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 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
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
206010012335 Dependence Diseases 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
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
230000003444 anaesthetic effect Effects 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
239000013065 commercial product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
WHQLQYRFIHPMNA-UHFFFAOYSA-N ethyl acetate;oxolane Chemical compound C1CCOC1.CCOC(C)=O WHQLQYRFIHPMNA-UHFFFAOYSA-N 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
230000003301 hydrolyzing effect Effects 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229960005181 morphine Drugs 0.000 description 1
210000003205 muscle Anatomy 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
239000002547 new drug Substances 0.000 description 1
229940127240 opiate Drugs 0.000 description 1
230000004526 pharmaceutical effect Effects 0.000 description 1
JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 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
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)

BG96513A 1989-12-21 1992-06-19 Заместени 4-фенил-4-пиперидинкарбоксамиди с локален обезболя- ващ и болкоуспокояващ ефект и метод за получаването им BG60912B1 (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SE8904298A SE8904298D0 (sv)	1989-12-21	1989-12-21	New compounds
PCT/SE1990/000818 WO1991009845A1 (fr)	1989-12-21	1990-12-17	4-phenyle-4-piperidinecarboxamides substitues avec effet anesthesique et analgesique local et procedes pour leur preparation

Publications (2)

Publication Number	Publication Date
BG96513A BG96513A (bg)	1993-12-24
BG60912B1 true BG60912B1 (bg)	1996-06-28

Family

ID=20377821

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG96513A BG60912B1 (bg)	1989-12-21	1992-06-19	Заместени 4-фенил-4-пиперидинкарбоксамиди с локален обезболя- ващ и болкоуспокояващ ефект и метод за получаването им

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 (15)

* 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
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
US6887889B2 (en) *	2001-04-12	2005-05-03	Pharmacopeia Drug Discovery, Inc.	Aryl and biaryl piperdines with MCH modulatory activity
KR20050087832A (ko) *	2002-12-13	2005-08-31	스미스클라인 비참 코포레이션	Ｃｃｒ5 길항제로서 피페리딘 유도체
AR063275A1 (es) *	2006-10-12	2009-01-14	Epix Delaware Inc	Compuestos de carboxamida, una composicion farmaceutica que los comprende y su uso en la preparacion de un medicamento para el tratamiento de enfermedades mediadas por la activacion de ccr2.
JP2011506466A (ja)	2007-12-11	2011-03-03	株式会社サイトパスファインダー	カルボキサミド化合物ならびにケモカイン受容体アゴニストとしてのそれらの使用
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
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
US9320908B2 (en)	2009-01-15	2016-04-26	Autonomic Technologies, Inc.	Approval per use implanted neurostimulator
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

Family Cites Families (9)

* 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
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
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 YU YU234690A patent/YU48086B/sh unknown
- 1990-12-12 SI SI9012346A patent/SI9012346B/sl not_active IP Right Cessation
- 1990-12-12 DZ DZ900223A patent/DZ1468A1/fr active
- 1990-12-17 WO PCT/SE1990/000818 patent/WO1991009845A1/fr active IP Right Grant
- 1990-12-17 CA CA002069608A patent/CA2069608C/fr not_active Expired - Fee Related
- 1990-12-17 IS IS3659A patent/IS1664B/is unknown
- 1990-12-17 EP EP91901571A patent/EP0506778B1/fr not_active Expired - Lifetime
- 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 ES ES91901571T patent/ES2087280T3/es not_active Expired - Lifetime
- 1990-12-17 DK DK91901571.9T patent/DK0506778T3/da active
- 1990-12-17 RO RO92-0832A patent/RO112864B1/ro unknown
- 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 AU AU69783/91A patent/AU647068B2/en not_active Ceased
- 1990-12-17 KR KR1019920701484A patent/KR0179382B1/ko not_active IP Right Cessation
- 1990-12-17 JP JP3501896A patent/JP2656152B2/ja not_active Expired - Fee Related
- 1990-12-17 DE DE69027221T patent/DE69027221T2/de not_active Expired - Fee Related
- 1990-12-17 UA UA5052485A patent/UA26403A/uk unknown
- 1990-12-20 EG EG74690A patent/EG19361A/xx active
- 1990-12-20 PT PT96303A patent/PT96303B/pt active IP Right Grant
- 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
- 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
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 BG BG96513A patent/BG60912B1/bg unknown
- 1992-06-19 RU SU925052485A patent/RU2039043C1/ru not_active IP Right Cessation
- 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/xx 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
IE904534A1 (en)	1991-07-03
HRP920591A2 (en)	1997-08-31
CN1037841C (zh)	1998-03-25
KR927003531A (ko)	1992-12-18
DE69027221D1 (de)	1996-07-04
US5360805A (en)	1994-11-01
ZA909903B (en)	1991-08-28
BR1100379A (pt)	1999-12-07
SI9012346A (sl)	1998-08-31
HK22997A (en)	1997-02-27
PL288409A1 (en)	1991-12-02
CN1053605A (zh)	1991-08-07
HU213110B (en)	1997-02-28
AU647068B2 (en)	1994-03-17
NO178858C (no)	1996-06-19
CZ658190A3 (en)	1993-01-13
FI100881B (fi)	1998-03-13
LV10949A (lv)	1995-12-20
YU48086B (sh)	1997-01-08
NO922380L (no)	1992-06-17
YU234690A (sh)	1993-10-20
LV5766A4 (lv)	1996-12-20
CA2069608A1 (fr)	1991-06-22
AU6978391A (en)	1991-07-24
IL96636A (en)	1994-11-28
JPH05502869A (ja)	1993-05-20
IS1664B (is)	1997-07-04
SI9012346B (sl)	1999-08-31
PT96303B (pt)	1998-07-31
IL96636A0 (en)	1991-09-16
LT4005B (en)	1996-07-25
NZ236293A (en)	1992-10-28
DK0506778T3 (da)	1996-10-07
EG19361A (en)	1994-12-30
EP0506778B1 (fr)	1996-05-29
FI922806A0 (fi)	1992-06-17
IE74855B1 (en)	1997-08-13
HU9202044D0 (en)	1992-09-28
DE69027221T2 (de)	1996-10-10
ES2087280T3 (es)	1996-07-16
FI922806A (fi)	1992-06-17
HRP920591B1 (en)	1998-12-31
WO1991009845A1 (fr)	1991-07-11
IS3659A7 (is)	1991-06-22
CA2069608C (fr)	2001-07-10
NO178858B (no)	1996-03-11
DZ1468A1 (fr)	2004-09-13
EP0506778A1 (fr)	1992-10-07
UA26403A (uk)	1999-08-30
SG46413A1 (en)	1998-02-20
ATE138650T1 (de)	1996-06-15
BG96513A (bg)	1993-12-24
PT96303A (pt)	1991-09-30
RO112864B1 (ro)	1998-01-30
KR0179382B1 (ko)	1999-03-20
SK658190A3 (en)	1996-08-07
JP2656152B2 (ja)	1997-09-24
LV5766B4 (lv)	1997-06-20
SA91110209B1 (ar)	2004-05-08
SE8904298D0 (sv)	1989-12-21
PL163591B1 (pl)	1994-04-29
LV10949B (en)	1996-06-20
NO922380D0 (no)	1992-06-17
HUT64518A (en)	1994-01-28
SK278283B6 (en)	1996-08-07
CZ278035B6 (en)	1993-07-14
US5227389A (en)	1993-07-13
RU2039043C1 (ru)	1995-07-09
LTIP1731A (en)	1995-07-25

Publication	Publication Date	Title
BG60912B1 (bg)	1996-06-28	Заместени 4-фенил-4-пиперидинкарбоксамиди с локален обезболя- ващ и болкоуспокояващ ефект и метод за получаването им
EP1858867B1 (fr)	2009-01-07	Derives trifluoromethylbenzamide et leurs utilisations therapeutiques
US5965734A (en)	1999-10-12	Processes and intermediates for preparing 2-substituted piperidine stereoisomers
KR101108222B1 (ko)	2012-02-08	진통 작용을 가진 인다졸아마이드
US4822895A (en)	1989-04-18	3-aminoazetidine, its salts and intermediates of synthesis
EP3643704B1 (fr)	2020-12-16	Nouveaux intermediaires pour la preparation de l hydrochloride de remifentanil
JP2720167B2 (ja)	1998-02-25	アルキレンジアミン誘導体
WO1989000159A1 (fr)	1989-01-12	Derives d'acides amines cycliques, leurs sels, compositions pharmaceutiques les contenant et leur procede de preparation
KR100245980B1 (ko)	2000-04-01	호모바닐릭아미드 유도체 및 이의 제조방법
JPH0160026B2 (fr)	1989-12-20
DE3207241A1 (de)	1983-09-01	Neue indol-derivate, verfahren zu ihrer herstellung und pharmazeutische praeparate, die diese verbindungen enthalten
CS217957B2 (cs)	1983-02-25	Způsob výroby nových cis popřípadě trans 2-aminocyklohexankarboxylových nebo cis popřípadě trans 2-aminocykIopentankarboxylových.kyselin
DE1112984B (de)	1961-08-24	Verfahren zur Herstellung von Pyrazolonderivaten
EP0134889A2 (fr)	1985-03-27	Acides cyclohexanecarboxyliques et leurs dérivés comme agents antiarrhythmiques
DD259189A5 (de)	1988-08-17	Verfahren zur herstellung neuer hydropyridin-derivate