DE2004200A1 - Neue basisch trisubstituierte Pyrimido-[5,4] pyrimidine und Verfahren zu ihrer Herstellung - Google Patents

Neue basisch trisubstituierte Pyrimido-[5,4] pyrimidine und Verfahren zu ihrer Herstellung

Info

Publication number: DE2004200A1
Authority: DE; Germany
Prior art keywords: pyrimido; pyrimidine; dimorpholino; radicals; deep3
Prior art date: 1970-01-30
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

DE19702004200

Other languages

German (de)

English (en)

Inventor

Berthold Dr Mueller

Josef Dipl-Chem Dr Nickl

Josef Dipl-Chem Dr Roch

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Boehringer Ingelheim Pharma GmbH and Co KG

Original Assignee

Dr Karl Thomae GmbH

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1970-01-30

Filing date

1970-01-30

Publication date

1971-08-12

1970-01-30 Application filed by Dr Karl Thomae GmbH filed Critical Dr Karl Thomae GmbH

1970-01-30 Priority to DE19702004200 priority Critical patent/DE2004200A1/de

1971-01-19 Priority to ES387408A priority patent/ES387408A0/es

1971-01-28 Priority to NL7101119A priority patent/NL7101119A/xx

1971-01-29 Priority to BE762326A priority patent/BE762326A/fr

1971-01-29 Priority to ZA710580A priority patent/ZA71580B/xx

1971-01-29 Priority to FR7103037A priority patent/FR2081470A1/fr

1971-01-29 Priority to IL36098A priority patent/IL36098A0/xx

1971-08-12 Publication of DE2004200A1 publication Critical patent/DE2004200A1/de

Status Pending legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims description 10
238000000034 method Methods 0.000 title claims description 8
150000003230 pyrimidines Chemical class 0.000 title 1
125000004432 carbon atom Chemical group C* 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 11
JOZPEVMCAKXSEY-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine Chemical class N1=CN=CC2=NC=NC=C21 JOZPEVMCAKXSEY-UHFFFAOYSA-N 0.000 claims description 11
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
239000011630 iodine Substances 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 4
239000007800 oxidant agent Substances 0.000 claims description 4
CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims description 3
239000013543 active substance Substances 0.000 claims description 3
239000003638 chemical reducing agent Substances 0.000 claims description 3
238000001640 fractional crystallisation Methods 0.000 claims description 3
239000000825 pharmaceutical preparation Substances 0.000 claims description 3
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 3
238000000926 separation method Methods 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
230000002401 inhibitory effect Effects 0.000 claims description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 2
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical group [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
-1 2-chloro-4,6-dimorpholino-pyrimido [5,4-d] pyrimidine Chemical compound 0.000 description 23
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
238000002844 melting Methods 0.000 description 17
230000008018 melting Effects 0.000 description 17
238000004519 manufacturing process Methods 0.000 description 16
239000000243 solution Substances 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 12
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000011347 resin Substances 0.000 description 5
229920005989 resin Polymers 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
229920001592 potato starch Polymers 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000011049 filling Methods 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000829 suppository Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
KRGXWTOLFOPIKV-UHFFFAOYSA-N 3-(methylamino)propan-1-ol Chemical compound CNCCCO KRGXWTOLFOPIKV-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
235000013871 bee wax Nutrition 0.000 description 2
239000012166 beeswax Substances 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000008298 dragée Substances 0.000 description 2
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
239000008187 granular material Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
229940057847 polyethylene glycol 600 Drugs 0.000 description 2
229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
239000001267 polyvinylpyrrolidone Substances 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
239000012286 potassium permanganate Substances 0.000 description 2
235000010199 sorbic acid Nutrition 0.000 description 2
239000004334 sorbic acid Substances 0.000 description 2
229940075582 sorbic acid Drugs 0.000 description 2
235000002906 tartaric acid Nutrition 0.000 description 2
239000011975 tartaric acid Substances 0.000 description 2
GBAXGHVGQJHFQL-UHFFFAOYSA-N 1-(2-hydroxyethylamino)propan-2-ol Chemical compound CC(O)CNCCO GBAXGHVGQJHFQL-UHFFFAOYSA-N 0.000 description 1
XWNSFEAWWGGSKJ-UHFFFAOYSA-N 4-acetyl-4-methylheptanedinitrile Chemical compound N#CCCC(C)(C(=O)C)CCC#N XWNSFEAWWGGSKJ-UHFFFAOYSA-N 0.000 description 1
JXPVNGYAUWESOK-UHFFFAOYSA-N CSC1=NC2=C(C=N1)N=C(N=C2N2CCOCC2)N2CCOCC2 Chemical compound CSC1=NC2=C(C=N1)N=C(N=C2N2CCOCC2)N2CCOCC2 JXPVNGYAUWESOK-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
239000004153 Potassium bromate Substances 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 0.000 description 1
238000007654 immersion Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229940094037 potassium bromate Drugs 0.000 description 1
235000019396 potassium bromate Nutrition 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- 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
- C07D487/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

DE19702004200 1970-01-30 1970-01-30 Neue basisch trisubstituierte Pyrimido-[5,4] pyrimidine und Verfahren zu ihrer Herstellung Pending DE2004200A1 (de)

Priority Applications (7)

Application Number	Priority Date	Filing Date	Title
DE19702004200 DE2004200A1 (de)	1970-01-30	1970-01-30	Neue basisch trisubstituierte Pyrimido-[5,4] pyrimidine und Verfahren zu ihrer Herstellung
ES387408A ES387408A0 (es)	1970-01-30	1971-01-19	Procedimiento para la preparacion de nuevas pirimido (5,4-d) pirimidinas.
NL7101119A NL7101119A (fr)	1970-01-30	1971-01-28
BE762326A BE762326A (fr)	1970-01-30	1971-01-29	Nouvelles pyrimido (5,4-d)pyrimidines basiquement trisubstituees et procedes pour les fabriquer
ZA710580A ZA71580B (en)	1970-01-30	1971-01-29	Improvements relating to basically trisubstituted pyrimido(5,4-d)pyrimidines
FR7103037A FR2081470A1 (en)	1970-01-30	1971-01-29	Pyrimidopyrimidines with cardiac and circulatory activity
IL36098A IL36098A0 (en)	1970-01-30	1971-01-29	Trisubstituted pyrimido (5,4-d) pyrimidines,their preparation and pharmaceutical compositions containing them

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19702004200 DE2004200A1 (de)	1970-01-30	1970-01-30	Neue basisch trisubstituierte Pyrimido-[5,4] pyrimidine und Verfahren zu ihrer Herstellung

Publications (1)

Publication Number	Publication Date
DE2004200A1 true DE2004200A1 (de)	1971-08-12

Family

ID=5760960

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19702004200 Pending DE2004200A1 (de)	1970-01-30	1970-01-30	Neue basisch trisubstituierte Pyrimido-[5,4] pyrimidine und Verfahren zu ihrer Herstellung

Country Status (7)

Country	Link
BE (1)	BE762326A (fr)
DE (1)	DE2004200A1 (fr)
ES (1)	ES387408A0 (fr)
FR (1)	FR2081470A1 (fr)
IL (1)	IL36098A0 (fr)
NL (1)	NL7101119A (fr)
ZA (1)	ZA71580B (fr)

1970
- 1970-01-30 DE DE19702004200 patent/DE2004200A1/de active Pending
1971
- 1971-01-19 ES ES387408A patent/ES387408A0/es active Pending
- 1971-01-28 NL NL7101119A patent/NL7101119A/xx unknown
- 1971-01-29 IL IL36098A patent/IL36098A0/xx unknown
- 1971-01-29 BE BE762326A patent/BE762326A/fr unknown
- 1971-01-29 FR FR7103037A patent/FR2081470A1/fr active Pending
- 1971-01-29 ZA ZA710580A patent/ZA71580B/xx unknown

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
US-Patent 3 322 755

Also Published As

Publication number	Publication date
IL36098A0 (en)	1971-03-24
ES387408A0 (es)	1973-05-16
FR2081470A1 (en)	1971-12-03
ZA71580B (en)	1971-11-24
NL7101119A (fr)	1971-08-03
BE762326A (fr)	1971-07-29

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