FI114473B - Förfarande för framställning av terapeutiskt användbara kinuklidinderivat - Google Patents
Förfarande för framställning av terapeutiskt användbara kinuklidinderivat Download PDFInfo
- Publication number
- FI114473B FI114473B FI930262A FI930262A FI114473B FI 114473 B FI114473 B FI 114473B FI 930262 A FI930262 A FI 930262A FI 930262 A FI930262 A FI 930262A FI 114473 B FI114473 B FI 114473B
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- Prior art keywords
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—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
-
- 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
-
- 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]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
-
- 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)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Control Of Electric Motors In General (AREA)
- Soft Magnetic Materials (AREA)
- Paper (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Claims (5)
1 R3 I I , R R3 tai 15 /—rTY^HCHiRl m r3 20 jossa kaavassa Y on (CH2)m, jossa m on kokonaisluku 1-3, tai Y on ryhmä, jolla on kaava . * •'VWi -w> :¾ 25 W ···. ( ) (-j> p on kokonaisluku 0-1; 30. on happi, rikki, amino, N- (C1-3) -alkyyliamino tai — (CH2) n- ja n on nolla, yksi tai kaksi; ·;· R1 on sykloalkyyli, jossa on 5 - 7 hiiliatomia, : ’·· pyrrolyyli, tienyyli, pyridyyli, fenyyli tai substituoitu fenyyli, jolloin mainittu substituoitu fenyyli on substitu- 35 oitu 1-3 substituentilla, jotka on valittu fluorista, kloorista, bromista, trifluorimetyylistä, 1-3 hiiliatomia 114473 sisältävästä alkyylistä, 1-3 hiiliatomia sisältävästä alkoksista, karboksista, alkoksikarbonyylistä, jossa on 1 -3 hiiliatomia alkoksiosuudessa, ja bentsyylioksikarbonyy-listä ja o 5. on furyyli, tienyyli, pyridyyli, indolyyli, bi- fenyyli, fenyyli tai substituoitu fenyyli, jolloin mainittu substituoitu fenyyli on substituoitu yhdellä tai kahdella substituentilla, jotka on valittu fluorista, kloorista, bromista, trifluorimetyylistä, 1-3 hiiliatomia sisältä-10 västä alkyylistä, 1-3 hiiliatomia sisältävästä alkoksista, karboksista, alkoksikarbonyylistä, jossa on 1 - 3 hiiliatomia alkoksiosuudessa, ja bentsyylioksikarbonyylistä; ja R3 on tienyyli, fenyyli, fluorifenyyli, kloori-15 fenyyli tai bromifenyyli; tunnettu siitä, että (A) (a) saatetaan yh diste, jolla on kaava R1CH2NH2, jossa R1 on edellä määritelty, reagoimaan (i) yhdisteen kanssa, jolla on kaava 20 X R2 τ' i 25 Y 'N *3 jossa Y, R2 ja R3 ovat edellä määriteltyjä, tai ^ 30 (ii) yhdisteen kanssa, jolla on kaava \ ^ j*2 v u. 35 R3 69 1 1 4473 jossa Z, R2 ja R3 ovat edellä määriteltyjä, tai (iii) yhdisteen kanssa, jolla on kaava 5 ^ R3 10 2 · 3 jossa p, R ja R ovat edellä määriteltyjä, ja sen j älkeen (b) pelkistetään tuote, joka on saatu vaiheen (A) 15 (a) kohdassa (i) , (ii) tai (iii), jolloin saadaan kaavan (I), (II) tai (III) mukainen yhdiste, tai (B) (a) yhdiste, jolla on kaava R2MgX, jossa R2 on edellä määritelty ja X on kloori, fluori, bromi tai jodi, saatetaan reagoimaan 20 (i) yhdisteen kanssa, jolla on kaava :j » CCC r3 jossa Y ja R3 ovat edellä määriteltyjä, jolloin 30 saadaan kaavan (I1) mukainen yhdiste, tai (ii) yhdisteen kanssa, jolla on kaava 35 \ R3 114473 jossa Z ja R3 ovat edellä määriteltyjä, jolloin saadaan kaavan (V) mukainen yhdiste, tai (iii) yhdisteen kanssa, jolla on kaava 5 C / III" 10 3 R3 jossa p ja R3 ovat edellä määriteltyjä, jolloin saadaan kaavan (III') mukainen yhdiste, ja sen jälkeen (b) tuotteen, joka on saatu vaiheen (B)(a) kohdissa 15 (i) , (ii) tai (iii) , annetaan reagoida kaavan R1CH2NH2 mu kaisen yhdisteen kanssa, jossa R1 on määritelty edellä, (c) vaiheesta (B)(b) saatu tuote pelkistetään, jolloin saadaan kaavan (I) , (II) tai (III) mukainen yhdiste, ja 20 haluttaessa näin saatu kaavan (I), (II) tai (III) mukainen yhdiste muutetaan farmaseuttisesti hyväksyttäväksi suolaksi. • > * * s > · * I I 71 1 1 4473 Förfarande för framställning av terapeutiskt an- vändbara kinuklidinderivat med formeln (I), (il) eller 5 (III) eller farmaceutiskt godtagbara syraadditionssalter därav, ^ ^ NHCHjR' ^-NHCHZR1 z0ti
10. V/ "
1 R3 H , R3 eller -KHCH.R1 ,s /=&f m R3 20. vilken formel Y är (CH2)m, väri m är ett heltal 1-3, eller Y är en grupp med formeln , ’ » 1 ·ΛΛΛ1 ·ννν 25 / \ (J) p är ett heltal 0 - 1; Z är syre, svavel, amino, N- (C1-3) -alkylamino eller 30 -(CH2)n- och n är 0, 1 eller 2; R1 är cykloalkyl med 5-7 kolatomer, pyrrolyl, *;1 tienyl, pyridyl, fenyl eller substituerad fenyl, varvid ; nämnda substituerade fenyl är substituerad med 1-3 sub- stituenter, valda bland fluor, klor, brom, trifluormetyl, 35 alkyl med 1-3 kolatomer, alkoxi med 1-3 kolatomer, kar- 114473 boxi, alkoxikarbonyl med 1-3 kolatomer i alkoxidelen, och bensyloxikarbonyl; och R2 är furyl, tienyl, pyridyl, indolyl, bifenyl, fenyl eller substituerad fenyl, varvid nämnda substituerade 5 fenyl är substituerad med en eller tvä substituenter, valda bland fluor, klor, brom, trifluormetyl, alkyl med 1-3 kolatomer, alkoxi med 1-3 kolatomer, karboxi, alkoxikarbonyl med 1-3 kolatomer i alkoxidelen och bensyloxikarbonyl; och
10 R3 är tienyl, fenyl, fluorfenyl, klorfenyl eller bromfenyl; kännetecknat därav, att man (A) (a) om-sätter en förening med formeln R1CH2NH2, väri R1 är säsom ovan definierats, med 15 (i) en förening med formeln
20 Y R3 ; · väri Y, R2 och R3 är säsom ovan definierats, eller ' (ii) en förening med formeln 25 : r3 * ♦ » , väri Z, R2 och R3 är säsom ovan definierats, eller (iii) en förening med formeln '·’ 35 1 1 4473 Ζ--ty 2 ηι' 5 Ρ R3 väri ρ, R2 och R3 är säsom ovan definierats, och därefter 10 (b) reducerar produkten, som erhällits i punkt (i) , (ii) eller (iii) i steg (A) (a) för erhällande av en före-ning med formeln (I), (II) eller (III), eller (B) (a) omsätter en förening med formeln R2MgX, väri R2 är säsom ovan definierats och X är klor, fluor, brom 15 eller jod, med (i) en förening med formeln 20 \ _ ( . I" N ^ : R3 25 väri Y och R3 är säsom ovan definierats för erhäl- lande av en förening med formeln (1'), eller (ii) en förening med formeln 30 _ / \ K iv : \ A /V ’ R3 35 väri Z och R3 är säsom ovan definierats för erhäl lande av en förening med formeln (V), eller 114473 (iii) en förening med formeln , /“tsT <λ vA R3 väri p ooh R3 är säsom ovan definierats för erhäl-10 lande av en förening med formeln (III'), och darefter b) omsätter produkten, som erhällits i punkt (i), (ii) eller (iii) i steg (B) (a), med en förening, som har formeln R1CH2NH2, där R är säsom ovan definierats, och darefter 15 (c) reducerar produkten, som erhällits i steg (B)(b) för erhällande av en förening med formeln (I), (II) eller (III), och om sä önskas, omvandlar den sä erhällna föreningen med formeln (I), (II) eller (III) tili ett farmaceutiskt 20 godtagbart sait. » i *
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55744290A | 1990-07-23 | 1990-07-23 | |
| US55744290 | 1990-07-23 | ||
| PCT/US1991/003369 WO1992001688A1 (en) | 1990-07-23 | 1991-05-14 | Quinuclidine derivatives |
| US9103369 | 1991-05-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI930262A FI930262A (fi) | 1993-01-22 |
| FI930262A0 FI930262A0 (fi) | 1993-01-22 |
| FI114473B true FI114473B (sv) | 2004-10-29 |
Family
ID=24225412
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI930262A FI114473B (sv) | 1990-07-23 | 1993-01-22 | Förfarande för framställning av terapeutiskt användbara kinuklidinderivat |
Country Status (25)
| Country | Link |
|---|---|
| US (5) | US5422354A (sv) |
| EP (1) | EP0540526B1 (sv) |
| JP (1) | JP2514137B2 (sv) |
| CN (1) | CN1058405A (sv) |
| AT (1) | ATE116317T1 (sv) |
| AU (1) | AU660416B2 (sv) |
| BR (1) | BR9106665A (sv) |
| CA (1) | CA2086434C (sv) |
| DE (1) | DE69106365T2 (sv) |
| DK (1) | DK0540526T3 (sv) |
| ES (1) | ES2065691T3 (sv) |
| FI (1) | FI114473B (sv) |
| GR (1) | GR3015144T3 (sv) |
| HU (1) | HUT62584A (sv) |
| IE (1) | IE65000B1 (sv) |
| IL (1) | IL98860A (sv) |
| MX (1) | MX9100308A (sv) |
| MY (1) | MY107157A (sv) |
| NO (1) | NO302172B1 (sv) |
| NZ (1) | NZ239063A (sv) |
| PL (1) | PL167568B1 (sv) |
| PT (1) | PT98393B (sv) |
| WO (1) | WO1992001688A1 (sv) |
| YU (1) | YU128091A (sv) |
| ZA (1) | ZA915727B (sv) |
Families Citing this family (74)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUT62584A (en) * | 1990-07-23 | 1993-05-28 | Pfizer | Process for producing quinuclidine derivatives |
| US5716965A (en) * | 1991-05-22 | 1998-02-10 | Pfizer Inc. | Substituted 3-aminoquinuclidines |
| DE9290083U1 (de) * | 1991-06-20 | 1994-02-17 | Pfizer Inc., New York, N.Y. | Fluoralkoxybenzylamino-Derivate von stickstoffhaltigen Heterocyclen |
| TW202432B (sv) * | 1991-06-21 | 1993-03-21 | Pfizer | |
| EP0607164B1 (en) * | 1991-09-26 | 2002-05-02 | Pfizer Inc. | Fused tricyclic nitrogen containing heterocycles as substance p receptor antagonists |
| WO1993010073A1 (en) * | 1991-11-12 | 1993-05-27 | Pfizer Inc. | Acyclic ethylenediamine derivatives as substance p receptor antagonists |
| ES2164657T3 (es) * | 1992-05-18 | 2002-03-01 | Pfizer | Derivados aza-biciclicos puenteados como antagonistas de la sustancia p. |
| US5688804A (en) * | 1992-08-04 | 1997-11-18 | Pfizer Inc. | 3-Benzylamino-2-phenyl-piperidine derivatives as substance P receptor antagonists |
| DE69331103T2 (de) * | 1992-08-19 | 2002-03-14 | Pfizer Inc., New York | Substituierte benzylamin-stickstoff enthaltende nichtaromatische heterocyclen |
| ES2147759T3 (es) * | 1992-12-10 | 2000-10-01 | Pfizer | Heterociclos no aromaticos sustituidos con aminometileno y uso como antagonistas de la sustancia p. |
| US5830854A (en) * | 1992-12-14 | 1998-11-03 | Merck Sharp & Dohme, Limited | Method of treating cystic fibrosis using a tachykinin receptor antagonist |
| US5340826A (en) * | 1993-02-04 | 1994-08-23 | Pfizer Inc. | Pharmaceutical agents for treatment of urinary incontinence |
| US5393762A (en) * | 1993-06-04 | 1995-02-28 | Pfizer Inc. | Pharmaceutical agents for treatment of emesis |
| EP0655246A1 (en) * | 1993-11-30 | 1995-05-31 | Pfizer Inc. | Substance P antagonists for the treatment of disorders caused by helicobacter pylori or other spiral urease-positive gram-negative bacteria |
| FR2725900B1 (fr) * | 1994-10-21 | 1997-07-18 | Sanofi Sa | Utilisation d'antagonistes des recepteurs nk1 pour la preparation de medicaments a action cardioregulatrice |
| IL116249A (en) * | 1994-12-12 | 2003-07-06 | Pfizer | Nk-1 receptor antagonists for the treatment of neuronal damage and stroke |
| GB9502582D0 (en) * | 1995-02-10 | 1995-03-29 | Smithkline Beecham Plc | Novel process |
| GB9510459D0 (en) | 1995-05-24 | 1995-07-19 | Zeneca Ltd | Bicyclic amines |
| CA2251851A1 (en) * | 1996-05-13 | 1997-11-20 | Roger Salmon | Bicyclic amines as insecticides |
| AU3784997A (en) * | 1996-08-09 | 1998-03-06 | Eisai Co. Ltd. | Benzopiperidine derivatives |
| GB9623944D0 (en) * | 1996-11-15 | 1997-01-08 | Zeneca Ltd | Bicyclic amine derivatives |
| GB9624114D0 (en) * | 1996-11-20 | 1997-01-08 | Zeneca Ltd | Pesticidal bicyclic amine derivatives |
| GB9624611D0 (en) | 1996-11-26 | 1997-01-15 | Zeneca Ltd | Bicyclic amine compounds |
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| AU7723300A (en) | 1999-09-27 | 2001-04-30 | Georgetown University | Novel tropane analogs |
| CA2324116A1 (en) * | 1999-10-25 | 2001-04-25 | Susan Beth Sobolov-Jaynes | Nk-1 receptor antagonists and eletriptan for the treatment of migraine |
| KR100885986B1 (ko) | 1999-11-03 | 2009-03-03 | 에이엠알 테크놀로지, 인크. | 노르에피네프린, 도파민 및 세로토닌의 재흡수를 방지하기위한 아릴 및 헤테로아릴 치환된테트라하이드로이소퀴놀린 및 이들의 용도 |
| US7163949B1 (en) | 1999-11-03 | 2007-01-16 | Amr Technology, Inc. | 4-phenyl substituted tetrahydroisoquinolines and use thereof |
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| US20020049211A1 (en) * | 2000-09-06 | 2002-04-25 | Sobolov-Jaynes Susan Beth | Combination treatment for depression and anxiety |
| EP1192952A3 (en) * | 2000-09-28 | 2003-03-26 | Pfizer Products Inc. | Combination, for treating depression and anxiety, containing an NK-3 receptor antagonist and a CNS penetrant NK-1 receptor antagonist |
| KR101389246B1 (ko) | 2004-07-15 | 2014-04-24 | 브리스톨-마이어스스퀴브컴파니 | 아릴- 및 헤테로아릴-치환된 테트라히드로이소퀴놀린, 및 이것의 노르에피네프린, 도파민 및 세로토닌의 재흡수를 차단하기 위한 용도 |
| ATE550019T1 (de) | 2005-05-17 | 2012-04-15 | Merck Sharp & Dohme | Cis-4-ä(4-chlorophenyl)sulfonylü-4-(2,5- difluorophenyl)cyclohexanepropansäure zur behandlug von krebs |
| JP5258561B2 (ja) | 2005-07-15 | 2013-08-07 | アルバニー モレキュラー リサーチ， インコーポレイテッド | アリール置換およびヘテロアリール置換テトラヒドロベンズアゼピンならびにノルエピネフリン、ドーパミンおよびセロトニンの再取り込みを遮断するためのその使用 |
| US8293900B2 (en) | 2005-09-29 | 2012-10-23 | Merck Sharp & Dohme Corp | Acylated spiropiperidine derivatives as melanocortin-4 receptor modulators |
| GB0603041D0 (en) | 2006-02-15 | 2006-03-29 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| EP2083831B1 (en) | 2006-09-22 | 2013-12-25 | Merck Sharp & Dohme Corp. | Method of treatment using fatty acid synthesis inhibitors |
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| JP5319518B2 (ja) | 2007-04-02 | 2013-10-16 | Ｍｓｄ株式会社 | インドールジオン誘導体 |
| JP5501227B2 (ja) | 2007-06-27 | 2014-05-21 | メルク・シャープ・アンド・ドーム・コーポレーション | ヒストンデアセチラーゼ阻害剤としての４−カルボキシベンジルアミノ誘導体 |
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| EP2584903B1 (en) | 2010-06-24 | 2018-10-24 | Merck Sharp & Dohme Corp. | Novel heterocyclic compounds as erk inhibitors |
| US8518907B2 (en) | 2010-08-02 | 2013-08-27 | Merck Sharp & Dohme Corp. | RNA interference mediated inhibition of catenin (cadherin-associated protein), beta 1 (CTNNB1) gene expression using short interfering nucleic acid (siNA) |
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| US2455949A (en) * | 1947-06-02 | 1948-12-14 | Parke Davis & Co | Dialkylaminoalkyl benzahydryl ethers and salts thereof |
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| US4246201A (en) * | 1979-06-11 | 1981-01-20 | Alfa Farmaceutici, S.P.A. | Substituted N-(3-phenylthiopropyl)-3,3-diphenyl-propylamines possessing pharmacological activity |
| MX18467A (es) * | 1988-11-23 | 1993-07-01 | Pfizer | Agentes terapeuticos de quinuclidinas |
| UA41251C2 (uk) * | 1990-01-04 | 2001-09-17 | Пфайзер, Інк. | Гідровані азотвмісні гетероциклічні сполуки, похідні піперидину, фармацевтична композиція та спосіб пригнічення активності речовини р в організмі |
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| HUT62584A (en) * | 1990-07-23 | 1993-05-28 | Pfizer | Process for producing quinuclidine derivatives |
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1991
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