FI85491B - Foerfarande foer framstaellning av nya terapeutiskt anvaendbara fosfonsyraderivat. - Google Patents
Foerfarande foer framstaellning av nya terapeutiskt anvaendbara fosfonsyraderivat. Download PDFInfo
- Publication number
- FI85491B FI85491B FI873503A FI873503A FI85491B FI 85491 B FI85491 B FI 85491B FI 873503 A FI873503 A FI 873503A FI 873503 A FI873503 A FI 873503A FI 85491 B FI85491 B FI 85491B
- Authority
- FI
- Finland
- Prior art keywords
- formula
- compound
- dimethyl
- pyridine
- dihydro
- Prior art date
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- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000001680 trimethoxyphenyl group Chemical group 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (13)
1. Förfarande för framställning av nya terapeutiskt användbara fosfonsyraderivat och farmaceutiskt godtagbara 5 salter och soivat av föreningarna och salterna med formeln I 10 ,R\ 0 χ2 3R / °N|1 (I) 'sy i i *6 CH^SACH3
15. H väri var och en av R1, R2, R3, R4, R5 och R6, vilka kan vara lika eller olika, är väte eller C1_4-alkyl; 20 nägondera av X1 och X2 är nitro, fluor, klor, difluormetoxi eller trifluormetyl och den andra är väte, eller X1 och X2 är klor; och Y är Ar1 /
25 -A-N \ 2 (ΟΗ2)βΑΓ2 väri A är C2_6-alkylen, vardera Ar1 och Ar2, vilka kan vara lika eller olika, är fenyl, som kan vara substituerad med 30 klor, fluor eller C^-alkoxi, och m är ett heltal 0-4, eller Y är / \ /Arl -A-N NCH \ / XAr2 36 8 5 491 väri A, Ar1 och Ar2 är som ovan angivits dä X1 är väte och X2 är difluormetoxi, eller dä bäde X1 och X2 är klor; kännetecknat därav, att man a) reagerar en förening med formeln 5 a1 x2 χ1
10 R /[ 0 I (II) R5 ' 6 C(0) R I CH3 15 väri R1, R2, R3, R4, R5, R6, X1 och X2 är som ovan angivits, med en förening med formeln NH2 C=CH (III)
20 CH3 X C02Y väri Y är som ovan angivits; eller b) reagerar följande tre utgängsmaterial 25 i 2r *17 0 n X1 nh r^/^3 V^x2 CH3 C°2Y
30 R5 R6 CHO väri R1, R2, R3, R4, R5, R6, X1, X2 och Y är som ovan angivits, med varandra, eller 35 c) reagerar följande tvä utgängsmaterial 37 8 5 491 λ^\ Ρ CH CO,Y r4/\ /\ ''c' 2 S^V·0 ίΗ2 I R o6 C=NH C(0) R I I CH3 CH3 10 väri R1, R2, R3, R4, R5, R6, X1, X2 och Y är som ovan angi-vits, med varandra, eller d) reagerar följande tre utgängsmaterial 15 i?h n h°xc=ch r4>( pch2cck3 caf Xco2Y 20 /Τ'- 0 CHO *5 1‘ väri R1, R2, R3, R4, R5, R6, X1, X2 och Y är som ovan angi-vits, med varandra, eller 25 e) reagerar följande tre utgängsmaterial i närvaro av en α-halogenalkanonsyra R5 „6 CH (N Z)2 R v / 38 85491 väri R1, R2, R3, R4, R5, R6, x1, x2 och Y är som ovan angi-vits och Z är -O- eller -CH2-; och, ifall önskvärt, omvandlar den resulterande föreningen med formeln I till dess farmaceutiskt godtagba-5 ra sait, och eventuellt omvandlar föreningen med formeln I eller saltet tili ett soivat.
2. Förfarande enligt patentkravet 1, känne-t e c k n a t därav, att man framställer en förening med formeln 10 vNO, C^\T°S γ A ,P co,CH,CH-N \!y/
15 CHsli CH, J H 3 eller ett farmaceutiskt godtagbart sait därav. 20
3. Förfarande enligt patentkravet 1, känne- t e c k n a t därav, att man framställer en förening med formeln .N°2 ex *X~ /XX C02CH2CH2N^O) _ CH3 V_0 jT Y CH2-@> chX^ ch*
30. H J väri solvent betecknar bensen eller toluen.
4. Förfarande enligt patentkravet 1, känne-t e c k n a t därav, att man framställer en förening med 35 formeln 39
? 5 Ί 91 ex CH3^-°li Y /7Λ · syre . c Λ P%^_ CO-CH-CH-N X^/ solvent c,jVo' 1Ϊ N CH, J H J väri solvent betecknar etanol eller acetonitril. 10 5. Förfarande enligt patentkravet 1, k ä n n e - t e c k n a t därav, att man framställer 2-(4-difenylmetyl-l-piperazinyl)etyl-5-(2,2-dimetylpropy-lendioxifosfinyl )-2, 6-dlmetyl-l, 4-dlhydro-4-( 2,3-diklor-fenyl)-pyridin-3-karboxylat, 15 3- [4-bis( 4-fluorfenyl )metyl-l-piperazinyl )propyl-5-( 2,2- dimetylpropylendioxifosf inyl )-2,6-dimetyl-l,4-dihydro-4-( 2,3-diklorfenyl)pyridin-3-karboxylat, 1- metyl-2-(N-bensyl-N-fenylamino)etyl-5-(1,1,3,3-tetrame-tylpropylendioxifosfinyl)-2,6-dimetyl-l,4-dihydro-4-(3- 20 nitrofenyl)pyridin-3-karboxylat, 2- (N-bensyl-N-fenylamino)etyl-5-(1,1,3,3-tetrametylpropy-lendioxifosfinyl)-2,6-dimetyl-l,4-dihydro-4-(3-nitrofe-nyl)pyridin-3-karboxylat, 1- metyl-2 -(N-bensyl-N-fenylamino )etyl-5- [ 1 (R), 3( R) -dime-25 tyylpropylendioxifosfinyl]-2, 6-dimetyl-l, 4-dihydro-4-( 2,3- diklorfenyl)pyridin-3-karboxylat, 2- (N-bensyl-N-fenylamino)etyl-5- [ 1 (R), 3(R)-dimetylpropy-lendioxifosfinyl]-2,6-dimetyl-l,4-dihydro-4-(3-nitrofenyl )pyridin-3-karboxylat, 30 2-(N,N-difenylamino)etyl-5-( 2,2-dimetylpropylendioxifosfi-nyl )-2,6-dimetyl-l, 4-dihydro-4-( 2,3-diklorfenyl )pyridin- 3- karboxylat, 3-(4-difenylmetyl-l-piperazinyl )propyl-5-( 2,2-dimetylpropylendioxifosf inyl)-2, 6-dimetyl-l,4-dihydro-4-(2,3-diklor-35 fenyl)pyridin-3-karboxylat, 40 85491 2- [4-bis( 4-f luorfenyl )metyl-l-piperazinyl] propyl- 5-( 2,2-dimetylpropylendioxifosf inyl )-2,6-dimetyl-l, 4-dihydro-4-(2,3-diklorfenyl)pyridin-3-karboxylat, 1- metyl-2-(N-bensy1-N-fenylamino)ety1-5-(2,2-dimetylprop- 5 ylendioxifosfinyl)-2,6-dimetyl-l,4-dihydro-4-(2,3-diklor fenyl )pyridin-3-karboxylat eller 2- (4-difenylmetyl-l-piperazinyl)etyl-5-(2,2-dimetylpropy-lendioxifosfinyl )-2, 6-dimetyl-l,4-dihydro-4-(2-difluorme- 10 toxifenylpyridin-3-karboxylat eller ett farmaceutiskt godtagbart salt eller soivat därav, eller ett soivat av saltet.
Applications Claiming Priority (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61011255A JPH0655751B2 (ja) | 1986-01-22 | 1986-01-22 | ジヒドロピリジンホスホン酸環状エステル |
| JP1125586 | 1986-01-22 | ||
| JP1275586 | 1986-01-23 | ||
| JP1275586 | 1986-01-23 | ||
| US06/851,158 US4885284A (en) | 1986-01-22 | 1986-04-14 | Dihydropyridine-5-phosphonic acid cyclic propylene ester |
| US85115886 | 1986-04-14 | ||
| JP28015986 | 1986-11-25 | ||
| JP28015986 | 1986-11-25 | ||
| PCT/JP1987/000032 WO1987004439A1 (en) | 1986-01-22 | 1987-01-20 | Dihydropyridine-5-phosphonic acid cyclic propylene ester |
| JP8700032 | 1987-01-20 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI873503A FI873503A (fi) | 1987-08-12 |
| FI873503A0 FI873503A0 (fi) | 1987-08-12 |
| FI85491B true FI85491B (fi) | 1992-01-15 |
| FI85491C FI85491C (sv) | 1992-04-27 |
Family
ID=27455571
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI873503A FI85491C (sv) | 1986-01-22 | 1987-08-12 | Förfarande för framställning av nya terapeutiskt användbara fosfonsyra derivat |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0230944B1 (sv) |
| CN (1) | CN1016063B (sv) |
| AR (1) | AR248142A1 (sv) |
| BG (1) | BG60236B1 (sv) |
| DE (1) | DE3761662D1 (sv) |
| DK (1) | DK168821B1 (sv) |
| FI (1) | FI85491C (sv) |
| GR (2) | GR3000478T3 (sv) |
| HU (1) | HU196605B (sv) |
| IL (1) | IL81315A (sv) |
| WO (1) | WO1987004439A1 (sv) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2528706B2 (ja) * | 1988-05-30 | 1996-08-28 | ゼリア新薬工業株式会社 | ジヒドロピリジン化合物の製剤組成物 |
| CA1334752C (en) * | 1988-08-02 | 1995-03-14 | Ryozo Sakoda | Drug effect-enhancing agent for antitumor drug |
| JP2850376B2 (ja) * | 1988-08-02 | 1999-01-27 | 日産化学工業株式会社 | 抗癌剤薬効増強剤 |
| KR100457273B1 (ko) * | 1996-03-18 | 2005-04-08 | 닛산 가가쿠 고교 가부시키 가이샤 | 에포니디핀염산염제제의제조방법 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59161392A (ja) | 1983-03-04 | 1984-09-12 | Nippon Shinyaku Co Ltd | ジヒドロピリジン誘導体及びその製法 |
| JPS6069089A (ja) | 1983-09-26 | 1985-04-19 | Nissan Chem Ind Ltd | ジヒドロピリジン−５−ホスホネ−ト誘導体およびその製造法 |
| DE3477669D1 (en) | 1983-09-26 | 1989-05-18 | Nissan Chemical Ind Ltd | Dihydropyridine-5-phosphonic acid cyclic ester |
| EP0141221A1 (en) | 1983-09-26 | 1985-05-15 | Nissan Chemical Industries Ltd. | 1,4-Dihydropyridine-5-phosphonic acid ester |
| JPS60248693A (ja) | 1984-04-19 | 1985-12-09 | Nippon Shinyaku Co Ltd | ピリジン誘導体及び製法 |
-
1987
- 1987-01-14 CN CN87100286.8A patent/CN1016063B/zh not_active Expired
- 1987-01-19 EP EP87100602A patent/EP0230944B1/en not_active Expired
- 1987-01-19 DE DE8787100602T patent/DE3761662D1/de not_active Expired - Lifetime
- 1987-01-20 WO PCT/JP1987/000032 patent/WO1987004439A1/en active IP Right Grant
- 1987-01-20 HU HU87768A patent/HU196605B/hu not_active IP Right Cessation
- 1987-01-20 IL IL81315A patent/IL81315A/xx not_active IP Right Cessation
- 1987-01-21 AR AR87306539A patent/AR248142A1/es active
- 1987-08-03 BG BG080825A patent/BG60236B1/bg unknown
- 1987-08-12 FI FI873503A patent/FI85491C/sv not_active IP Right Cessation
- 1987-08-17 DK DK428087A patent/DK168821B1/da not_active IP Right Cessation
-
1990
- 1990-05-07 GR GR90400281T patent/GR3000478T3/el unknown
- 1990-10-31 GR GR89300192T patent/GR890300192T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU589485B2 (en) | 1989-10-12 |
| GR890300192T1 (en) | 1990-10-31 |
| BG60236B2 (en) | 1994-01-24 |
| BG60236B1 (bg) | 1994-01-24 |
| FI873503A (fi) | 1987-08-12 |
| HUT44570A (en) | 1988-03-28 |
| DK168821B1 (da) | 1994-06-20 |
| DK428087A (da) | 1987-08-17 |
| AR248142A1 (es) | 1995-06-30 |
| DK428087D0 (da) | 1987-08-17 |
| HU196605B (en) | 1988-12-28 |
| WO1987004439A1 (en) | 1987-07-30 |
| CN87100286A (zh) | 1988-01-13 |
| IL81315A (en) | 1991-11-21 |
| IL81315A0 (en) | 1987-08-31 |
| FI85491C (sv) | 1992-04-27 |
| FI873503A0 (fi) | 1987-08-12 |
| GR3000478T3 (en) | 1991-06-28 |
| DE3761662D1 (de) | 1990-03-15 |
| EP0230944B1 (en) | 1990-02-07 |
| AU6763587A (en) | 1987-07-23 |
| EP0230944A1 (en) | 1987-08-05 |
| CN1016063B (zh) | 1992-04-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: NISSAN CHEMICAL INDUSTRIES, LTD. |