SI9300513B - Kvarterni bazični amidi, postopek za njihovo pripravo in farmacevtski sestavki, v katerih so prisotni - Google Patents
Kvarterni bazični amidi, postopek za njihovo pripravo in farmacevtski sestavki, v katerih so prisotni Download PDFInfo
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- SI9300513B SI9300513B SI9300513A SI9300513A SI9300513B SI 9300513 B SI9300513 B SI 9300513B SI 9300513 A SI9300513 A SI 9300513A SI 9300513 A SI9300513 A SI 9300513A SI 9300513 B SI9300513 B SI 9300513B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- 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
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- 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
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- 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
- A61P25/06—Antimigraine agents
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- 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]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
Claims (14)
1 PATENTNI ZAHTEVKI 1. Kvartemi bazičen amid s formulo R Q i -N-CH2-C-CH2-CH«j-Am ^ , A^ * Ar' v kateri Ar predstavlja fenilno skupino, kije nesubstituirana ali substituirana z enim ali več substituenti, izbranimi izmed naslednjih, kot so: F; Cl; Br; I; CN; OH; NH2; NH-CONH2; N02; CONH2; CF3; Ci-Ci0-alkil; alkenil z 2 do 10 atomi ogljika; alkinil z 2 do 10 atomi ogljika; cikloalkil s 3 do 8 atomi ogljika; bicikloalkil s 4 do 11 atomi ogljika; hidroksialkil z 1 do 5 atomi ogljika; alkoksi z 1 do 10 atomi ogljika; alkoksialkil z 2 do 10 atomi ogljika; alkoksialkoksialkil z do 10 atomi ogljika; alkoksialkoksi z 2 do 10 atomi ogljika; alkeniloksi z 2 do 10 atomi ogljika; alkeniloksialkil z do 10 atomi ogljika; alkeniloksi z 2 do 10 atomi ogljika; alkeniloksialkil s 3 do 10 atomi ogljika; cikloalkoksi s 3 do 8 atomi ogljika; alkiltio z 1 do 10 atomi ogljika; alkiltioalkil z 2 do 10 atomi ogljika; acilamino z 1 do 7 atomi ogljika; acilaminoalkil z 2 do 8 atomi ogljika; aciloksi z 1 do 6 atomi ogljika; alkoksikarbonil z 2 do 5 atomi ogljika; cikloalkoksikarbonil s 4 do 8 atomi ogljika; alkilaminokarbonilamino z 2 do 4 atomi ogljika; dialkilaminokarbonilamino s 3 do 7 atomi ogljika; (1-pirolidinojkarbonilamino; cikloalkilaminokarbonilamino s 4 do 8 atomi ogljika; alkilaminokarbonilaminoalkil s 3 do 9 atomi ogljika; dialkilaminokarbonil-aminoalkil s 4 do 11 atomi ogljika; (l-pirolidino)karbonilaminoetil; (1-piperidinojkarbonilaminoetil; cikloalkilaminokarbonilaminoalkil s 5 do 12 atomi ogljika; alkoksikarbonilaminoalkil s 3 do 12 atomi ogljika; cikloalkoksi-karbonilaminoalkil s 5 do 12 atomi ogljika; karbamoilalkil z 2 do 5 atomi ogljika; alkilaminokarbonilalkil s 3 do 9 atomi ogljika; dialkilaminokarbonil-alkil s 4 do 11 atomi ogljika; (l-pirolidino)karbonilmetil; (1-piperidinojkarbonilmetil; (1 -piperidinojkarboniletil; cikloalkilaminokarbonil- 2 alkil s 5 do 12 atomi ogljika; alkilaminokarbonilalkoksi s 3 do 10 atomi ogljika; dialkilaminokarbonilalkoksi s 4 do 10 atomi ogljika; (piperidinil-l)karbonilmetoksi; cikloalkilaminokarbonilalkoksi s 5 do 11 atomi ogljika; ali Ar predstavlja 1- ali 2-naftilno skupino, 1-, 2-, 3-, 4-, 5-, 6-, 7-indenilno skupino; katerih ena ali več vezi je lahko hidrogeniranih, pri čemer so lahko te skupine nesubstituirane ali substituirane z enim ali več substituenti, izbranimi izmed naslednjih, kot so: halogen, alkilna, fenilna, ciano, hidroksialkilna, hidroksi, alkoksi, okso, alkilkarbonilamino, alkoksikarbonilna in tioalkilna skupina, v katerih so Ci-C4-alkili; piridilna, tiadiazolilna, indolilna, indazolilna, imidazolilna, benzimidazolilna, kinolilna, benzotriazolilna, benzofuranilna, benzotienilna, benzotiazolilna, benzizotiazolilna, izokinolilna, benzoksazolilna, benzoksazinilna, benzodioksinilna, izoksazolilna, benzopiranilna, tiazolilna, tienilna, furilna, piranilna, kromenilna, izobenzofuranilna, pirolilna, pirazolilna, pirazinilna, pirimidinilna, piridazinilna, indolizinilna, ftalazinilna, kinazolinilna, akridinilna, izotiazolilna, izokromanilna, kromanilna skupina, katerih ena ali več dvojnih vezi je lahko hidrogeniranih, pri čemer so lahko te skupine nesubstituirane ali substituirane z enim ali več substituenti, izbranimi izmed naslednjih, kot so: alkilna, fenilna, ciano, hidroksialkilna, hidroksi, alkilkarbonilamino, alkoksikarbonilna, in tioalkilna skupina, v kateri so Ci-C4 -alkih; T predstavlja direktno vez, hidroksimetilensko skupino, alkoksimetilensko skupino, katere alkoksi skupina je s CrC4, ali Ci-C5-alkilensko skupino; Ar' predstavlja fenil, ki je nesubstituiran ali je enkrat ali večkrat substituiran z enim od substituentov, izbranim izmed naslednjih, kot so: atom halogena, trifluormetil, CrC4-alkoksi, CrC4-alkil, pri čemer so ti substituenti enaki ali različni; tienil; benzotienil; nafti 1 ali indolil; R predstavlja vodik; Ci-C4-alkil; ®-(CrC4)alkoksi(C2-C4)alkil; ali co-(C2-C4)alkanoiloksi(C2-C4)alkil; Q predstavlja vodik; ali pa Q in R skupaj tvorita 1,2-etilensko, 1,3-propilensko ali 1,4-butilensko skupino; 3 Am® predstavlja ostanek
kjer X], X2, Χ3 skupaj in z atomom dušika, na katerega so vezani, tvorijo azabicikličen sistem, izbran izmed l-azoniabiciklo[2.2.1]heptana in 1-azoniabiciklo[2.2.2]oktana, v danem primeru substituiran s fenilno ali benzilno skupino; A' je farmacevtsko sprejemljiv anion.
2. Kvarterni bazičen amid s formulo (I) po zahtevku 1, označen s tem, da Am® predstavlja l-azoniabiciklo[2.2.2]oktansko skupino ali 4-fenil-l-azoniabiciklo[2.2.2]oktansko skupino.
3. Kvarterni bazičen amid po zahtevku 1 ali 2 s formulo I R Q i Ar-T^O-N-CH2<:-CH2-CH2-Am®,AG (I) Ar’ v kateri so Ar, T, Ar', R in Q, kot je definirano v zahtevku 1, označen s tem, daje Am® ostanek Θ x2-n- x3 v formuli (I) in je ostanek azabicikličnega ali azatricikličnega sistema, izbran izmed naslednjih, kot so: (a) l-azoniabiciklo[2.2.2]oktan (b) 4-fenil-l-azoniabiciklo[2.2.2]oktan, 4 ter je A' farmacevtsko sprejemljiv anion.
4. Kvartemi bazičen amid s formulo I po kateremkoli od zahtevkov 1 do 3, označen s tem, da so T, R, Ar' in Q, kot je definirano za (I), Am® je 1-azoniabiciklo[2.2.2]oktanski ali 4-fenil-l-azoniabiciklo[2.2.2]oktanski ostanek, Arje fenil, substituiran s CrC4-alkoksi, in je A" farmacevtsko sprejemljiv anion.
5. Kvartemi bazičen amid s formulo iPr-0 R’ Q'
R" . A® (Γ) kjer sta R' in Q' metil in vodik oz. 2-acetoksietil in vodik; ali R' in Q skupaj tvorita 1,3-propilensko skupino, R" je vodik ali fenilna skupina in je A' farmacevtsko sprejemljiv anion.
6. Kvartemi bazičen amid s formulo
iPr-0 kjer je A' farmacevtsko sprejemljiv anion.
7. Kvartemi bazičen amid po kateremkoli od zahtevkov 1 do 6, označen s tem, daje A' izbran izmed klorida, bromida, jodida, hidrogensulfata, metansulfonata, paratoluensulfonata in acetata. 5 8. (+)-l-[2-[3-(3,4-diklorofenil)-l-[(3-izopropoksifenil)acetil]piperidin-3-il]etil]-4-fenil-1 -azoniabiciklo [2.2.2] oktan-klorid.
9. Postopek za pripravo spojin s formulo (I), označen s tem, da derivat s formulo R Q I I Ar-T-C0-N-CH2-C-CH2-CH2-0-Y (II) Ar' kjer je Y katerakoli odstranljiva skupina, prednostno metansulfonil ali benzensulfonil, obdelujemo s cikličnim terc.aminom s formulo f1 X2 ~ N (III) X3 kjer Xj, X2 in X3 skupaj z atomom dušika, na katerega so vezani, tvorijo azabiciklični ali azatriciklični sistem, v danem primeru substituiran s fenilno skupino, v polarnem aprotičnem topilu pri temperaturi med sobno temperaturo in 120 °C in nato po potrebi izmenjamo anion dobljene kvarteme soli z drugim farmacevtsko sprejemljivim anionom.
10. Postopek po zahtevku 8, označen s tem, da je odhodna skupina OY metansulfonatna ali benzensulfonatna skupina.
11. Postopek po enem od zahtevkov 8 ali 9, označen s tem, da cikličen terc.amin (III) izberemo izmed
6
12. Farmacevtski sestavek, označen s tem, daje spojina s formulo (I) po zahtevku 1 prisotna kot aktivna snov.
13. Farmacevtski sestavek po zahtevku 12 v obliki dozirne enote, označen s tem, da aktivno snov pomešamo z vsaj enim farmacevtskim nosilcem.
14. Sestavek po zahtevku 13, označen s tem, da vsebuje 0,5 do 1000 mg aktivne snovi.
15. Sestavek po zahtevku 14, označen s tem, da vsebuje od 2,5 do 250 mg aktivne snovi.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9212083A FR2696178B1 (fr) | 1992-09-30 | 1992-09-30 | Amides basiques quaternaires, procédé pour leur préparation et compositions pharmaceutiques en contenant. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SI9300513A SI9300513A (en) | 1994-06-30 |
| SI9300513B true SI9300513B (sl) | 2002-02-28 |
Family
ID=9434374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9300513A SI9300513B (sl) | 1992-09-30 | 1993-09-30 | Kvarterni bazični amidi, postopek za njihovo pripravo in farmacevtski sestavki, v katerih so prisotni |
Country Status (27)
| Country | Link |
|---|---|
| EP (1) | EP0591040B1 (sl) |
| JP (2) | JP2857041B2 (sl) |
| KR (1) | KR100279084B1 (sl) |
| CN (1) | CN1036652C (sl) |
| AT (1) | ATE176469T1 (sl) |
| AU (1) | AU674875B2 (sl) |
| BR (1) | BR9303982A (sl) |
| CA (1) | CA2107432C (sl) |
| CZ (1) | CZ287272B6 (sl) |
| DE (1) | DE69323375T2 (sl) |
| DK (1) | DK0591040T3 (sl) |
| ES (1) | ES2130238T3 (sl) |
| FI (1) | FI114474B (sl) |
| FR (1) | FR2696178B1 (sl) |
| GR (1) | GR3030000T3 (sl) |
| HU (2) | HU215848B (sl) |
| IL (1) | IL107158A0 (sl) |
| MX (1) | MX9306024A (sl) |
| MY (1) | MY108881A (sl) |
| NO (1) | NO304888B1 (sl) |
| NZ (1) | NZ248821A (sl) |
| OA (1) | OA09869A (sl) |
| RU (1) | RU2120436C1 (sl) |
| SG (1) | SG47807A1 (sl) |
| SI (1) | SI9300513B (sl) |
| TW (1) | TW242625B (sl) |
| ZA (1) | ZA937276B (sl) |
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|---|---|---|---|---|
| US5583134A (en) * | 1992-09-30 | 1996-12-10 | Sanofi | 1-azoniabicyclo[2.2.2] octanes and pharmaceutical compositions in which they are present |
| FR2717802B1 (fr) * | 1994-03-25 | 1996-06-21 | Sanofi Sa | Nouveaux composés aromatiques, procédé pour leur préparation et compositions pharmaceutiques en contenant. |
| FR2717804B1 (fr) * | 1994-03-25 | 1996-06-21 | Sanofi Sa | Sels de composés hétéroaromatiques azotés substitués, procédé pour leur préparation et compositions pharmaceutiques en contenant. |
| NZ270985A (en) | 1994-04-29 | 1997-06-24 | Lilly Co Eli | Substituted benzimidazole derivatives; medicaments and preparation of medicaments |
| NZ289652A (en) | 1994-07-12 | 1998-05-27 | Lilly Co Eli | (r)-3-(1h-indol-3-yl)-1-[n-(2-methoxybenzyl)acetylamino]-2-[n-(2-(4-( piperidin-1-yl)piperidin-1-yl)acetyl)amino]propane dihydrochloride trihydrate; non-peptidyl tachykinin receptor antagonistic medicaments |
| FR2725900B1 (fr) * | 1994-10-21 | 1997-07-18 | Sanofi Sa | Utilisation d'antagonistes des recepteurs nk1 pour la preparation de medicaments a action cardioregulatrice |
| US6008223A (en) * | 1994-10-27 | 1999-12-28 | Zeneca Limited | Therapeutic compounds |
| GB9421709D0 (en) * | 1994-10-27 | 1994-12-14 | Zeneca Ltd | Therapeutic compounds |
| EP0714891A1 (en) * | 1994-11-22 | 1996-06-05 | Eli Lilly And Company | Heterocyclic tachykinin receptor antagonists |
| FR2729954B1 (fr) * | 1995-01-30 | 1997-08-01 | Sanofi Sa | Composes heterocycliques substitues, procede pour leur preparation et compositions pharmaceutiques les contenant |
| FR2729951B1 (fr) * | 1995-01-30 | 1997-04-18 | Sanofi Sa | Nouveaux composes heterocycliques, procede pour leur preparation et compositions pharmaceutiques en contenant |
| FR2729952B1 (fr) * | 1995-01-30 | 1997-04-18 | Sanofi Sa | Composes heterocycliques substitues, procede pour leur preparation et compositions pharmaceutiques les contenant |
| FR2751654B1 (fr) * | 1996-07-26 | 1998-10-23 | Sanofi Sa | Composes heterocycliques substitues, procede pour leur preparation et compositions pharmaceutiques les contenant |
| US5654316A (en) * | 1995-06-06 | 1997-08-05 | Schering Corporation | Piperidine derivatives as neurokinin antagonists |
| ES2191755T3 (es) * | 1995-06-06 | 2003-09-16 | Schering Corp | Compuestos heterociclicos bencenofusionados sustituidos como antagonistas de la neuroquinina. |
| FR2745811B1 (fr) * | 1996-03-07 | 1998-05-22 | Sanofi Sa | Glutarimide disubstitue procede pour sa preparation, et son utilisation |
| AU3149297A (en) * | 1996-05-24 | 1997-12-09 | Eli Lilly And Company | Methods of treating hypertension |
| US5691362A (en) * | 1996-06-05 | 1997-11-25 | Schering-Plough Corporation | Substituted benzene-fused hetero- and carbocyclics as nuerokinin antagonists |
| GB9617730D0 (en) * | 1996-08-23 | 1996-10-02 | Pfizer Ltd | Quarternary ammonium compounds |
| FR2759585B1 (fr) * | 1997-02-17 | 1999-06-11 | Sanofi Sa | Formulations pharmaceutiques presentees sous forme seche pour l'administration orale d'un compose ammonium quaternaire cyclique |
| FR2759584B1 (fr) * | 1997-02-17 | 1999-06-11 | Sanofi Sa | Composition pharmaceutique pour l'administration orale de composes heterocycliques sous forme ammonium quaternaire |
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| GB9712882D0 (en) * | 1997-06-18 | 1997-08-20 | Pfizer Ltd | Quaternary ammonium compounds |
| GB9716457D0 (en) * | 1997-08-04 | 1997-10-08 | Merck Sharp & Dohme | Therapeutic agents |
| GB9716463D0 (en) * | 1997-08-04 | 1997-10-08 | Merck Sharp & Dohme | Therapeutic agents |
| CA2298779A1 (en) * | 1997-08-04 | 1999-02-18 | Merck Sharp & Dohme Limited | Use of nk-1 receptor antagonists for treating aggressive behaviour disorders |
| CA2298777A1 (en) * | 1997-08-04 | 1999-02-18 | Merck Sharp & Dohme Limited | Use of nk-1 receptor antagonists for treating mania |
| GB9816897D0 (en) * | 1998-08-04 | 1998-09-30 | Merck Sharp & Dohme | Therapeutic use |
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| PL1910346T3 (pl) | 2005-07-19 | 2019-09-30 | Azevan Pharmaceuticals, Inc. | Beta-laktamowy antagonista wazopresyny fenyloalaniny, cysteiny i seryny |
| WO2008090117A1 (en) | 2007-01-24 | 2008-07-31 | Glaxo Group Limited | Pharmaceutical compositions comprising 3, 5-diamin0-6- (2, 3-dichl0phenyl) -l, 2, 4-triazine or r (-) -2, 4-diamino-5- (2, 3-dichlorophenyl) -6-fluoromethyl pyrimidine and an nk1 |
| UA105182C2 (ru) | 2008-07-03 | 2014-04-25 | Ньюрексон, Інк. | Бензоксазины, бензотиазины и родственные соединения, которые имеют ингибирующую nos активность |
| CN107007596A (zh) | 2010-07-01 | 2017-08-04 | 阿泽凡药物公司 | 用于治疗创伤后应激障碍的方法 |
| MX2021005502A (es) | 2014-03-28 | 2023-01-16 | Azevan Pharmaceuticals Inc | Composiciones y metodos para tratar enfermedades neurodegenerativas. |
| MY196804A (en) * | 2016-12-14 | 2023-05-03 | Beijing Showby Pharmaceutical Co Ltd | Class of bifunctional compounds with quaternary ammonium salt structure |
| EP3681871A4 (en) | 2017-09-15 | 2021-05-26 | Azevan Pharmaceuticals, Inc. | COMPOSITIONS AND METHODS OF TREATMENT OF BRAIN INJURY |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI97540C (fi) * | 1989-11-06 | 1997-01-10 | Sanofi Sa | Menetelmä terapeuttisesti käyttökelpoisten, aromaattisesti substituoitujen piperidiini- ja piperatsiinijohdannaisten valmistamiseksi |
| FR2666185B1 (fr) * | 1990-08-21 | 1992-12-04 | Sgs Thomson Microelectronics | Convertisseur analogique/numerique a interpolation. |
| IL99320A (en) * | 1990-09-05 | 1995-07-31 | Sanofi Sa | Arylalkylamines, their preparation and pharmaceutical preparations containing them |
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1992
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1993
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- 1993-09-28 EP EP93402362A patent/EP0591040B1/fr not_active Expired - Lifetime
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- 1993-09-30 BR BR9303982A patent/BR9303982A/pt not_active Application Discontinuation
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1995
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1997
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1999
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Effective date: 20100531 |