SI9012346B - Substituirani 4-fenil-4-piperidinkarboksamidi z lokalno-anestezijskim in analgetskim učinkom kot tudi postopki za njihovo pripravo - Google Patents
Substituirani 4-fenil-4-piperidinkarboksamidi z lokalno-anestezijskim in analgetskim učinkom kot tudi postopki za njihovo pripravo Download PDFInfo
- Publication number
- SI9012346B SI9012346B SI9012346A SI9012346A SI9012346B SI 9012346 B SI9012346 B SI 9012346B SI 9012346 A SI9012346 A SI 9012346A SI 9012346 A SI9012346 A SI 9012346A SI 9012346 B SI9012346 B SI 9012346B
- Authority
- SI
- Slovenia
- Prior art keywords
- formula
- compound
- compound according
- carbon atoms
- alkyl group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 3
- 238000002360 preparation method Methods 0.000 title claims abstract 3
- 230000000202 analgesic effect 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
- 239000003589 local anesthetic agent Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 11
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract 3
- 230000036592 analgesia Effects 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 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 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 238000002347 injection Methods 0.000 claims 2
- 239000007924 injection Substances 0.000 claims 2
- 238000007913 intrathecal administration Methods 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims 2
- 206010002091 Anaesthesia Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 230000037005 anaesthesia Effects 0.000 claims 1
- 230000003444 anaesthetic effect Effects 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 239000012467 final product Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 150000003839 salts 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 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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Cosmetics (AREA)
Claims (8)
1 PATENTNI ZAHTEVKI 1. Spojine s formulo IV R 1
označene s tem, da je v formuli Ri alkilna skupina z 2-6 atomi ogljika ali alkoksialkilna skupina R40(CH2)m-, kjer je R4 alkilna skupina z 1-4 atomi ogljika in je m 2-4, sta R2 in R3 enaka ali različna in je vsak alkilna skupina z do 6 atomi ogljika, ali R2 in R3 skupaj tvorita verigo (CH2)n, kjer je n 4-6, ali pa je eden od R2 in R3 vodik in je drugi nerazvejana ali razvejana alkilna skupina z 1-6 atomi ogljika, kot tudi njihove farmacevtsko sprejemljive soli.
2. Spojina po zahtevku 1, označena s tem, da so Ri, R2 in R3 alkilne skupine.
3. Spojina po zahtevku 2, označena s tem, daje Ri heksil, je R2 metil in je R3 etil.
4. Spojina po zahtevku 2, označena s tem, daje Ri heksil in sta R2 in R3 oba etil.
5. Farmacevtski pripravek za kontrolo blokade po epiduralni ali intratekalni poti, označen s tem, da vsebuje spojino po zahtevku 1 kot aktivno sestavino skupaj s tekočim razredčilom, primernim za injekcijo in da je v obliki za epiduralno ah intratekalno dajanje.
6. Farmacevtski pripravek za anestezijo in analgezijo, označen s tem, da vsebuje spojino po zahtevku 1 kot aktivno sestavino skupaj s tekočim razredčilom, primernim za injekcijo. 2
7. Uporaba spojine po zahtevku 1 za proizvodnjo farmacevtskega pripravka z anestezij skim in analgetskim učinkom.
8. Postopek za pripravo spojine s formulo IV po zahtevku 1, označen s tem, da: a) ester ali nitril s formulo I hidroliziramo v ustrezno kislino s formulo III, katero nato presnovimo z 1) oksalilkloridom in 2) ustreznim aminom, tako da dobimo končni produkt s formulo IV:
kjer so Rh R2 in R3 kot je definirano zgoraj v zahtevku 1 in je A -CN ali -CO2C2H5· ali b) spojino s formulo I, v kateri je A -CO2C2H5, presnovimo z aminom s formulo R2NH2, tako da dobimo spojino s formulo II, v kateri sta Ri in R2 kot je definirano zgoraj, se pravi spojino s formulo IV, v kateri sta R2 ali R3 vodik. 3
I II
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8904298A SE8904298D0 (sv) | 1989-12-21 | 1989-12-21 | New compounds |
| YU234690A YU48086B (sh) | 1989-12-21 | 1990-12-12 | Supstituisani 4-fenil-4-piperidinkarboksamid i postupak za njihovo dobijanje |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SI9012346A SI9012346A (sl) | 1998-08-31 |
| SI9012346B true SI9012346B (sl) | 1999-08-31 |
Family
ID=20377821
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9012346A SI9012346B (sl) | 1989-12-21 | 1990-12-12 | Substituirani 4-fenil-4-piperidinkarboksamidi z lokalno-anestezijskim in analgetskim učinkom kot tudi postopki za njihovo pripravo |
Country Status (40)
| Country | Link |
|---|---|
| US (2) | US5227389A (sl) |
| EP (1) | EP0506778B1 (sl) |
| JP (1) | JP2656152B2 (sl) |
| KR (1) | KR0179382B1 (sl) |
| CN (1) | CN1037841C (sl) |
| AT (1) | ATE138650T1 (sl) |
| AU (1) | AU647068B2 (sl) |
| BG (1) | BG60912B1 (sl) |
| BR (1) | BR1100379A (sl) |
| CA (1) | CA2069608C (sl) |
| CZ (1) | CZ278035B6 (sl) |
| DE (1) | DE69027221T2 (sl) |
| DK (1) | DK0506778T3 (sl) |
| DZ (1) | DZ1468A1 (sl) |
| EG (1) | EG19361A (sl) |
| ES (1) | ES2087280T3 (sl) |
| FI (1) | FI100881B (sl) |
| HK (1) | HK22997A (sl) |
| HR (1) | HRP920591B1 (sl) |
| HU (1) | HU213110B (sl) |
| IE (1) | IE74855B1 (sl) |
| IL (1) | IL96636A (sl) |
| IS (1) | IS1664B (sl) |
| LT (1) | LT4005B (sl) |
| LV (2) | LV10949B (sl) |
| NO (1) | NO178858C (sl) |
| NZ (1) | NZ236293A (sl) |
| PL (1) | PL163591B1 (sl) |
| PT (1) | PT96303B (sl) |
| RO (1) | RO112864B1 (sl) |
| RU (1) | RU2039043C1 (sl) |
| SA (1) | SA91110209B1 (sl) |
| SE (1) | SE8904298D0 (sl) |
| SG (1) | SG46413A1 (sl) |
| SI (1) | SI9012346B (sl) |
| SK (1) | SK658190A3 (sl) |
| UA (1) | UA26403A (sl) |
| WO (1) | WO1991009845A1 (sl) |
| YU (1) | YU48086B (sl) |
| ZA (1) | ZA909903B (sl) |
Families Citing this family (15)
| 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 |
| WO2002083134A1 (en) * | 2001-04-12 | 2002-10-24 | Pharmacopeia, Inc. | Aryl and biaryl piperidines used as mch antagonists |
| WO2004054974A2 (en) * | 2002-12-13 | 2004-07-01 | Smithkline Beecham Corporation | Piperidine derivatives as ccr5 antagonists |
| 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 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE96980C1 (sl) | ||||
| 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 DZ DZ900223A patent/DZ1468A1/xx active
- 1990-12-12 SI SI9012346A patent/SI9012346B/sl not_active IP Right Cessation
- 1990-12-12 YU YU234690A patent/YU48086B/sh unknown
- 1990-12-17 ES ES91901571T patent/ES2087280T3/es not_active Expired - Lifetime
- 1990-12-17 IS IS3659A patent/IS1664B/is unknown
- 1990-12-17 WO PCT/SE1990/000818 patent/WO1991009845A1/en active IP Right Grant
- 1990-12-17 AT AT91901571T patent/ATE138650T1/de not_active IP Right Cessation
- 1990-12-17 DK DK91901571.9T patent/DK0506778T3/da active
- 1990-12-17 CA CA002069608A patent/CA2069608C/en not_active Expired - Fee Related
- 1990-12-17 AU AU69783/91A patent/AU647068B2/en not_active Ceased
- 1990-12-17 UA UA5052485A patent/UA26403A/uk 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 DE DE69027221T patent/DE69027221T2/de not_active Expired - Fee Related
- 1990-12-17 RO RO92-0832A patent/RO112864B1/ro unknown
- 1990-12-17 KR KR1019920701484A patent/KR0179382B1/ko not_active IP Right Cessation
- 1990-12-17 EP EP91901571A patent/EP0506778B1/en not_active Expired - Lifetime
- 1990-12-17 JP JP3501896A patent/JP2656152B2/ja not_active Expired - Fee Related
- 1990-12-17 HU HU9202044A patent/HU213110B/hu unknown
- 1990-12-20 PT PT96303A patent/PT96303B/pt active IP Right Grant
- 1990-12-20 EG EG74690A patent/EG19361A/xx active
- 1990-12-21 US US07/633,246 patent/US5227389A/en not_active Expired - Lifetime
- 1990-12-21 PL PL90288409A patent/PL163591B1/pl not_active IP Right Cessation
- 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 SK SK6581-90A patent/SK658190A3/sk unknown
-
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/xx not_active IP Right Cessation
- 1997-04-30 BR BR1100379-0A patent/BR1100379A/pt active IP Right Grant
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| Date | Code | Title | Description |
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Effective date: 20060731 |