FI83222C - Foerfarande foer framstaellning av farmakologiskt verksamma karboxialkyldipeptider. - Google Patents
Foerfarande foer framstaellning av farmakologiskt verksamma karboxialkyldipeptider. Download PDFInfo
- Publication number
- FI83222C FI83222C FI813283A FI813283A FI83222C FI 83222 C FI83222 C FI 83222C FI 813283 A FI813283 A FI 813283A FI 813283 A FI813283 A FI 813283A FI 83222 C FI83222 C FI 83222C
- Authority
- FI
- Finland
- Prior art keywords
- carboxylic acid
- alanyl
- phenylpropyl
- substituted
- compound
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
- C07K5/0222—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2 with the first amino acid being heterocyclic, e.g. Pro, Trp
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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
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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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pyrrole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Apparatus For Disinfection Or Sterilisation (AREA)
- Saccharide Compounds (AREA)
Claims (2)
1. Menetelmä farmakologisesti vaikuttavien karboksialkyyli-dipeptidien valmistamiseksi, joiden kaava on
0 Rl R3 R< R5 0 H I I I I II . . R-C-C-NH-CH-C-N-C-C-R® (I) i II i R2 0 R7 tai sen farmaseuttisesti hyväksyttävä suola, jolloin seuraavissa substituenttien määritelmissä aryyli tai ar tarkoittaa fenyyliä tai naftyyliä, jossa kaavassa R on hydroksi tai alempi alkoksi ja R6 on hydroksi, alempi alkoksi, aryylioksi, aryyli-alempi alkoksi, amino, alempi alkyyliamino, aryy1i(ai empi alkyyli)amino tai substituoitu aryylioksi tai substituoitu aryyli-alempi alkoksi, Rl on vety, 1-10 hiiliatominen alkyyli, substituoitu alempi alkyyli, jossa substituentti on aryylioksi, substituoitu aryylioksi, amino, imidatsolyyli, indolyyli, alempi alkyylitio, aryylitio, substituoitu aryylitio, aryyli, substituoitu aryyli, aralkyylioksi, substituoitu aralkyylioksi, aralkyylitio tai substituoitu aralkyylitio, joissa mainittujen substituoitujen aryylioksi-, aryyliamino-, aryylitio-, aryyli-, aralkyylioksi-, aralkyylitioryhmän aryyli on substituoitu halogeenilla, alempi alkyylilla, hydroksi11 a, alempi alkoksilla, aminolla, aminome-tyylillä, karboksyy1i1lä, syanolla tai sulfamoyylillä; R2 ja R7, jotka voivat olla samanlaisia tai erilaisia, ovat vety tai alempi alkyyli; R3 on vety, alempi alkyyli, amino-(aiempi alkyyli), dimetyyliamino-(aiempi alkyyli), tai alempi alkyylitio(alempi alkyyli); R4 ja Rs muodostavat yhdessä ryhmän Q tai U, jolla ryhmällä Q on kaava R®X1 X2R* (CH2)p (CHa)q \ / 55 8 3 2 2 2 jossa X1 ja X* ovat toisistaan riippumatta o, S tai CH2, R® ja R® ovat toisistaan riippumatta alempi alkyyli, alempi alkenyyli, alempi alkynyyli, 3-8 hiiliatominen sykloalkyyli, hydroksi-(alempi alkyyli) tai -(CH2)nAr, jossa n on 0, 1, 2 tai 3 ja Ar on substituoimaton tai substituoitu fenyyli, furyyli, tienyyli tai pyridyyli, jolloin mainitut substituoidut fenyyli-, furyyli-, tienyyli- tai pyridyyliryhmät ovat substituoidut vähintään yhdellä ryhmällä, jotka toisistaan riippumatta on valittu seuraavista: Ci-C^-alkyyli, alempi alkoksi, alempi alkyylitio, halogeeni, CPs tai hydroksi,tai R® ja R® muodostavat yhdessä sillan W, jolloin W on yksinkertainen sidos tai mety-leenisilta, kun ainakin toinen ryhmistä X3- ja X2 on metyleeni, tai H on alkyleenisilta, jossa on 2 tai 3 hiiliatomia, ja edellyttäen, että jos X1 ja X2 tarkoittavat molemmat metyleeniä, täytyy ryhmän R® ja R® muodostaa alkyleenisi11 an W; p on 0, 1 tai 2, q on 0, 1 tai 2, edellyttäen, että p:n ja q:n summan on oltava 1, 2 tai 3, edellyttäen että, jos p on 0, täytyy ryhmän Xl ja X2 olla metyleeni, ja jolla ryhmällä U on kaava “ W - (CH2)p Mala), N / jossa W tarkoittaa samaa kuin edellä (lukuunottamatta, että W voi myös olla metyleenisilta, kun X1 ja X2 tarkoittavat happea tai rikkiä), X1 ja X2 tarkoittavat samaa kuin edellä, p on 0, 1 tai 2, q on 0, 1 tai 2, edellyttäen, että p:n ja q:n summa on 1 tai 2, ja edellyttäen, että jos p on 0, täytyy ryhmä X1 olla CH2, lukuunottamatta yhdistettä, jossa U on i ί » t 56 83222 Q (CH2)p (CH2)« jossa p on 0 tai 1 ja q on 1 ja tai R4 ja R* muodostavat yhdessä hiili- ja typpiatomin kanssa, : joihin ne ovat liittyneet, proliinirenkaan edellyttäen, että ; H1 on alempi alkyyli, joka on substituoitu aralkyylitiolla tai ) aralkyylioksilla, tunnettu siitä, että yhdiste valmistetaan sopivalla menetelmällä valittuna seuraavista menetelmistä (jolloin seu-raavissa kaavoissa R, R1, R2, R3, R4, R*, R« ja R? tarkoittavat samaa kuin kaavassa I ja sisältävät tarvittaessa suojauksen): a) kaavan I mukaisten yhdisteiden, joissa R2 on vety, valmis- j tamiseksi kondensoidaan pelkistävästä ketoyhdiste (XIII) dipeptidin (XIV) kanssa O Rl R30 R4 R5 O Il t * H I I il R-C-C=0+ H2NCHC -n-c-c-r6 -----> 1 R7 XIII XIV b) alkyloidaan dipeptidi (XIV) yhdisteen (XXII) avulla R3 O R4 R* Rl I II I I 1 h2n -ch-c-n-c - cor« + x - c - COR -----> I. R7 R2 XIV XXII 57 83222 jossa X on kloori, bromi, jodi, aikaanisulfonyy1ioksi tai areenisulfonyy1ioksi; c) kondensoidaan pelkistävästä aminoyhdiste (XVIII) ketoyhdis-teen (XIX) kanssa
0 Rl R3 0 R* R5 Il ! I tl I i R - C - C - NH2 +0=C-C-N-C0-R6 ----> I I I R2 R7 XVIII XIX d) alkyloidaan aminoyhdiste (XVIII) yhdisteen (XXIII) kanssa Rl R3 O R< R* l I li I i R - C - C - NH2 + X-CH-C-N-C- COR« ----> I H I i
0 R2 R7 XVIII XXIII jossa X on kloori, bromi, jodi, alkaanisulfonyylioksi tai areenisulfonyylioksi; e) kondensoidaan aminohappo (XXI) aminohapon (XVII) kanssa Rl R3 R« R5 li il RCO - C - NH - CH - COOH + HN - C - COR« ----> I ( l R2 R? XXI XVII minkä jälkeen tarvittaessa poistetaan suojaryhmät halutun tuotteen saamiseksi, ja haluttaessa muunnetaan näin saatu kaavan I mukainen yhdiste toiseksi kaavan I mukaiseksi yhdisteeksi ja haluttaessa valmistetaan sen suola ja haluttaessa eristetään parhaana pidetty isomeeri. 58 8 3 2 2 2
2. Patenttivaatimuksen 1 mukainen menetelmä, tunnettu siitä, että valmistettu yhdiste on l-[N-(l-karboetoksi-3-fenyylipropyyli)-(S)-alanyyli]-okta-hydrosyklopenta[b]pyrroli-karboksyylihappo; l-[N-(l-karboksi-3-fenyylipropyyli)-(S)-alanyyli]-oktahydro-sykiopenta(b)-pyrroli-2(S)-karboksyylihappo; 7-[N-(karboetoksi-3-fenyylipropyyli)-(S)-alanyyli]-l,4-ditia-7-atsaspiro[4,4]nonaani-8(S)-karboksyylihappo; 5-[N-(l-karboksietoksi-3-fenyylipropyyli)-(S)-alanyyli]-2,2-dimetyyli-okdtahydro-1,3-dioksolo[4,5-c]pyrroli-4(S)karbok-syy1ihappo; 7[N-(l-karboksi-3-fenyylipropyyli)-(S)-alanyyli-1,4-ditia-7-atsaspiro[4,4]nonaani-8(S)-karboksyylihappo.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US19988680A | 1980-10-23 | 1980-10-23 | |
US19988680 | 1980-10-23 | ||
US25848481A | 1981-04-28 | 1981-04-28 | |
US25848481 | 1981-04-28 |
Publications (3)
Publication Number | Publication Date |
---|---|
FI813283L FI813283L (fi) | 1982-04-24 |
FI83222B FI83222B (fi) | 1991-02-28 |
FI83222C true FI83222C (fi) | 1991-06-10 |
Family
ID=26895254
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI813283A FI83222C (fi) | 1980-10-23 | 1981-10-20 | Foerfarande foer framstaellning av farmakologiskt verksamma karboxialkyldipeptider. |
Country Status (28)
Country | Link |
---|---|
US (2) | US4818749A (fi) |
EP (1) | EP0050800B2 (fi) |
JP (1) | JPH01163197A (fi) |
KR (1) | KR880001843B1 (fi) |
AT (1) | ATE20469T1 (fi) |
AU (1) | AU554362B2 (fi) |
CA (1) | CA1341206C (fi) |
CY (1) | CY1469A (fi) |
DE (2) | DE3174844D1 (fi) |
DK (1) | DK161523C (fi) |
ES (1) | ES506414A0 (fi) |
FI (1) | FI83222C (fi) |
GR (1) | GR75059B (fi) |
HK (1) | HK36189A (fi) |
HU (1) | HU193146B (fi) |
IE (1) | IE53802B1 (fi) |
IL (1) | IL64085A (fi) |
KE (1) | KE3845A (fi) |
LU (1) | LU88621I2 (fi) |
MA (1) | MA19309A1 (fi) |
MY (1) | MY8700683A (fi) |
NL (1) | NL940001I2 (fi) |
NO (2) | NO164983C (fi) |
NZ (1) | NZ198702A (fi) |
OA (1) | OA06929A (fi) |
PH (1) | PH21916A (fi) |
PT (1) | PT73861B (fi) |
SG (1) | SG78188G (fi) |
Families Citing this family (144)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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US4508729A (en) * | 1979-12-07 | 1985-04-02 | Adir | Substituted iminodiacids, their preparation and pharmaceutical compositions containing them |
US4644008A (en) * | 1979-12-07 | 1987-02-17 | Adir | Perhydroindole-2-carboxylic acids as antihypertensives |
US4616030A (en) * | 1979-12-07 | 1986-10-07 | Adir | Perhydroindole-2-carboxylic acids as antihypertensives |
US4350704A (en) * | 1980-10-06 | 1982-09-21 | Warner-Lambert Company | Substituted acyl derivatives of octahydro-1H-indole-2-carboxylic acids |
EP0278530A3 (de) * | 1980-08-30 | 1989-08-02 | Hoechst Aktiengesellschaft | Aminosäurederivate, Verfahren zu ihrer Herstellung, diese enthaltende Mittel und deren Verwendung |
ATE20469T1 (de) * | 1980-10-23 | 1986-07-15 | Schering Corp | Carboxyalkyl-dipeptide, verfahren zu ihrer herstellung und diese enthaltende arzneimittel. |
US4906615A (en) * | 1980-12-18 | 1990-03-06 | Schering Corporation | Substituted dipeptides as inhibitors of enkephalinases |
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US4584285A (en) * | 1983-06-02 | 1986-04-22 | Schering Corporation | Antihypertensive agents |
FR2546886B2 (fr) * | 1983-06-06 | 1986-05-16 | Adir | Derives d'acides isoindoledicarboxyliques, leur preparation et compositions pharmaceutiques les contenant |
DE3322530A1 (de) * | 1983-06-23 | 1985-01-10 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von mono-, bi- und tricyclischen aminosaeuren |
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DE3333455A1 (de) * | 1983-09-16 | 1985-04-11 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung n-alkylierter dipeptide und deren estern |
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1981
- 1981-10-15 AT AT81108348T patent/ATE20469T1/de active
- 1981-10-15 DE DE8181108348T patent/DE3174844D1/de not_active Expired
- 1981-10-15 DE DE1995175012 patent/DE19575012I2/de active Active
- 1981-10-15 LU LU88621C patent/LU88621I2/fr unknown
- 1981-10-15 EP EP81108348A patent/EP0050800B2/en not_active Expired - Lifetime
- 1981-10-20 DK DK462581A patent/DK161523C/da not_active IP Right Cessation
- 1981-10-20 AU AU76614/81A patent/AU554362B2/en not_active Expired
- 1981-10-20 NZ NZ198702A patent/NZ198702A/en unknown
- 1981-10-20 CA CA000388336A patent/CA1341206C/en not_active Expired - Fee Related
- 1981-10-20 OA OA57524A patent/OA06929A/xx unknown
- 1981-10-20 FI FI813283A patent/FI83222C/fi not_active IP Right Cessation
- 1981-10-20 GR GR66307A patent/GR75059B/el unknown
- 1981-10-20 MA MA19511A patent/MA19309A1/fr unknown
- 1981-10-20 PH PH26366A patent/PH21916A/en unknown
- 1981-10-21 NO NO813546A patent/NO164983C/no not_active IP Right Cessation
- 1981-10-21 KR KR1019810004008A patent/KR880001843B1/ko active
- 1981-10-21 PT PT73861A patent/PT73861B/pt unknown
- 1981-10-21 IE IE2475/81A patent/IE53802B1/en not_active IP Right Cessation
- 1981-10-21 IL IL64085A patent/IL64085A/xx active IP Right Grant
- 1981-10-21 ES ES506414A patent/ES506414A0/es active Granted
- 1981-10-22 HU HU813078A patent/HU193146B/hu unknown
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1987
- 1987-11-04 US US07/117,008 patent/US4818749A/en not_active Expired - Lifetime
- 1987-12-30 MY MY683/87A patent/MY8700683A/xx unknown
-
1988
- 1988-09-28 US US07/250,300 patent/US4831157A/en not_active Expired - Lifetime
- 1988-11-09 JP JP63283542A patent/JPH01163197A/ja active Pending
- 1988-11-18 KE KE3845A patent/KE3845A/xx unknown
- 1988-11-21 SG SG781/88A patent/SG78188G/en unknown
-
1989
- 1989-05-04 HK HK361/89A patent/HK36189A/xx not_active IP Right Cessation
- 1989-07-21 CY CY1469A patent/CY1469A/xx unknown
-
1994
- 1994-01-26 NL NL940001C patent/NL940001I2/nl unknown
-
1995
- 1995-09-22 NO NO1995008C patent/NO1995008I1/no unknown
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