FI68400C - Foerfarande foer framstaellning av n-(4-(((2,4-diamino-6-pteridinyl)-metyl)metylamino)bensoyl)glutaminsyra - Google Patents
Foerfarande foer framstaellning av n-(4-(((2,4-diamino-6-pteridinyl)-metyl)metylamino)bensoyl)glutaminsyra Download PDFInfo
- Publication number
- FI68400C FI68400C FI812774A FI812774A FI68400C FI 68400 C FI68400 C FI 68400C FI 812774 A FI812774 A FI 812774A FI 812774 A FI812774 A FI 812774A FI 68400 C FI68400 C FI 68400C
- Authority
- FI
- Finland
- Prior art keywords
- diamino
- methylamino
- benzoyl
- methotrexate
- pteridinyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 21
- YFSVPBJUHQLTIQ-ZDUSSCGKSA-N (2s)-5-amino-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]-5-oxopentanoic acid Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(N)=O)C(O)=O)C=C1 YFSVPBJUHQLTIQ-ZDUSSCGKSA-N 0.000 title description 2
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 claims description 24
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 24
- 229960000485 methotrexate Drugs 0.000 claims description 20
- SDZKFWPFFHILFI-UHFFFAOYSA-N 6-(chloromethyl)pteridine-2,4-diamine;hydrochloride Chemical compound Cl.N1=C(CCl)C=NC2=NC(N)=NC(N)=C21 SDZKFWPFFHILFI-UHFFFAOYSA-N 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- CYNARAWTVHQHDI-UHFFFAOYSA-N (2,4-diaminopteridin-6-yl)methanol Chemical compound N1=C(CO)C=NC2=NC(N)=NC(N)=C21 CYNARAWTVHQHDI-UHFFFAOYSA-N 0.000 claims description 9
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 9
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 5
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 5
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 5
- -1 2,4-diamino-6-pteridinyl Chemical group 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 229930195712 glutamate Natural products 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 3
- 235000013922 glutamic acid Nutrition 0.000 claims description 3
- 239000004220 glutamic acid Substances 0.000 claims description 3
- FBOZXECLQNJBKD-UHFFFAOYSA-N methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-UHFFFAOYSA-N 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 239000003880 polar aprotic solvent Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000006386 neutralization reaction Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- RFHCIZRJBWSDRR-UHFFFAOYSA-N Br.BrCC1=NC2=NC=CN=C2C=N1 Chemical compound Br.BrCC1=NC2=NC=CN=C2C=N1 RFHCIZRJBWSDRR-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 3
- WHUUTDBJXJRKMK-GSVOUGTGSA-N D-glutamic acid Chemical compound OC(=O)[C@H](N)CCC(O)=O WHUUTDBJXJRKMK-GSVOUGTGSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- IMLOZVNPFFXWAQ-UHFFFAOYSA-N (5-amino-6-cyanopyrazin-2-yl)methyl acetate Chemical compound CC(=O)OCC1=CN=C(N)C(C#N)=N1 IMLOZVNPFFXWAQ-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- YKPQUSLRUFLVDA-UHFFFAOYSA-N $l^{2}-azanylmethane Chemical compound [NH]C YKPQUSLRUFLVDA-UHFFFAOYSA-N 0.000 description 1
- UFBUCKLNZUNJHS-JTQLQIEISA-N (2s)-2-[[4-(methylamino)benzoyl]amino]pentanedioic acid Chemical compound CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 UFBUCKLNZUNJHS-JTQLQIEISA-N 0.000 description 1
- IHJBYRAXZVHUGF-UHFFFAOYSA-N 6-(chloromethyl)pteridine-2,4-diamine Chemical compound N1=C(CCl)C=NC2=NC(N)=NC(N)=C21 IHJBYRAXZVHUGF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010000830 Acute leukaemia Diseases 0.000 description 1
- 229930195713 D-glutamate Natural products 0.000 description 1
- FBOZXECLQNJBKD-CYBMUJFWSA-N D-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-CYBMUJFWSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940034982 antineoplastic agent Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 150000003195 pteridines Chemical class 0.000 description 1
- PZRKPUQWIFJRKZ-UHFFFAOYSA-N pyrimidine-2,4,5,6-tetramine Chemical compound NC1=NC(N)=C(N)C(N)=N1 PZRKPUQWIFJRKZ-UHFFFAOYSA-N 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 101150005399 sod2 gene Proteins 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
- C07D475/06—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4
- C07D475/08—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4 with a nitrogen atom directly attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (8)
1. J ^' ^2 h2n ^ΙΓ^ΪΤ ch2
20 COOH V
1. Förfarande för framställning av N-[4-[[(2,4-diamino-6-pteri-dinyl)tnetyl]metylamino]bensoyl]glutaminsyra eller metotrexat 5 kännetecknat därav, att 2,4-diamino-6-hydroxi- metylpteridin med fortneln IV nh2 io n/^X^n^ch2oh h2n IV 15 omsättes med tionylklorid, varvid erhalles 2 ,4-diamino-6- klormetylpteridinhydroklorid med formeln I. nh2 20 /-N^^JCH.CI i jO HjN^Tr^ir 25 med vilken man alkylerar dietyl N-[4-(methylamino)bensoyl]_ glutamat med formeln II cooc2h5 ch3nh-/ O/-conhch( ch2 ) 2cooc2h5 30 '-' II 1 ett polärt aprotiskt lösningsraedel i närvaro av kalium-jodid, varefter den erhällna hydrojodiden av dietyl N-[4- 35 [[(2,4-diamino-6-pteridinyl)metyl]metylamino]bensoyl]~ glutamat med 68400 formeln III NH2 CH3 /-v COOC2H5
5. O >CONHCH(CH2)2COOC2H5 vO H2N N n III 10 hydrolyseras, antingen direkt eller efter neutralisation till föreningen III, varvid erhalles N-[4-[[(2,4-diamino-6-pteridinyl)™etyl]metylamino]bent8oyl]glutaminisyra (metotrexat) med formeln V 15 ^2 JL ^°°H N>1^\v/'N>sv£H2 N ( )—CONHCH
2. Förfarande enligt patentkravet 1 kännetecknat därav, att det polära aprotiska lösningsmedlet är dimetyl- 25 sulfoxid. 2 3 2 Förfarande enligt patentkravet 1 eller 2, kännetecknat därav, att man använder 1-5 mol kaliumjodid per mol 2,4-diamino-6-klormetylpteridinhydroklorid. 30
3 Förfarande enligt patentkravet 3, kännet ecknat därav, att man använder 4 mol kaliumjodid per mol 2,4- diamino-6-klormetylpteridinhydroklorid.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK390480 | 1980-09-12 | ||
| DK390480 | 1980-09-12 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI812774L FI812774L (fi) | 1982-03-13 |
| FI68400B FI68400B (fi) | 1985-05-31 |
| FI68400C true FI68400C (fi) | 1985-09-10 |
Family
ID=8128069
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI812774A FI68400C (fi) | 1980-09-12 | 1981-09-08 | Foerfarande foer framstaellning av n-(4-(((2,4-diamino-6-pteridinyl)-metyl)metylamino)bensoyl)glutaminsyra |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0048002A3 (sv) |
| CA (1) | CA1167844A (sv) |
| FI (1) | FI68400C (sv) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2590255B1 (fr) * | 1985-11-19 | 1987-12-24 | Rhone Poulenc Sante | Procede de preparation de derives de la pteridine |
| US9139592B2 (en) | 2010-06-14 | 2015-09-22 | Trt Pharma Inc. | Modulators of Nrf2 and uses thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1414752A (en) * | 1974-03-20 | 1975-11-19 | Inst Oncologic | Process for the preparation of diamino-pteridyl-methyl- methylamino-benzoyl-glutamic acid derivative |
| CH630380A5 (de) * | 1977-08-12 | 1982-06-15 | Lonza Ag | Verfahren zur herstellung von l-methotrexat. |
-
1981
- 1981-09-08 FI FI812774A patent/FI68400C/fi not_active IP Right Cessation
- 1981-09-11 CA CA000385687A patent/CA1167844A/en not_active Expired
- 1981-09-11 EP EP81107199A patent/EP0048002A3/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| FI812774L (fi) | 1982-03-13 |
| FI68400B (fi) | 1985-05-31 |
| EP0048002A2 (en) | 1982-03-24 |
| CA1167844A (en) | 1984-05-22 |
| EP0048002A3 (en) | 1982-06-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: ORION-YHTYMAE OY FERMION |