DE1285478B - Verfahren zur Herstellung von neuen 5, 6, 7, 8-Tetrahydropyrido-[4, 3-d]pyrimidinen - Google Patents
Verfahren zur Herstellung von neuen 5, 6, 7, 8-Tetrahydropyrido-[4, 3-d]pyrimidinenInfo
- Publication number
- DE1285478B DE1285478B DET21812A DET0021812A DE1285478B DE 1285478 B DE1285478 B DE 1285478B DE T21812 A DET21812 A DE T21812A DE T0021812 A DET0021812 A DE T0021812A DE 1285478 B DE1285478 B DE 1285478B
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- group
- methyl
- alkyl
- hydrogen atom
- Prior art date
- 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
Links
- 238000000034 method Methods 0.000 title claims description 5
- STXKJIIHKFGUCY-UHFFFAOYSA-N 5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Chemical class C1=NC=C2CNCCC2=N1 STXKJIIHKFGUCY-UHFFFAOYSA-N 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims 2
- -1 iminodipropionic acid ester Chemical class 0.000 claims description 78
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 235000005985 organic acids Nutrition 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000006228 Dieckmann condensation reaction Methods 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000001409 amidines Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000002585 base Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- RCFIDKPBGWQLTE-UHFFFAOYSA-N ethyl 1-methyl-2-oxopiperidine-3-carboxylate Chemical compound CCOC(=O)C1CCCN(C)C1=O RCFIDKPBGWQLTE-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 101000874172 Rattus norvegicus Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Proteins 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000006178 methyl benzyl group Chemical group 0.000 description 2
- NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- GVYBTSCEJAHEOW-UHFFFAOYSA-N 1,3,6-trimethyl-8,8-diphenyl-2,4,5,7-tetrahydropyrido[4,3-d]pyrimidine Chemical compound C1N(C)CN(C)C2=C1CN(C)CC2(C=1C=CC=CC=1)C1=CC=CC=C1 GVYBTSCEJAHEOW-UHFFFAOYSA-N 0.000 description 1
- WTYJBGQERCCGAD-UHFFFAOYSA-N 1-Methylguanidine sulfate (2:1) Chemical compound CN=C(N)N.CN=C(N)N.OS(O)(=O)=O WTYJBGQERCCGAD-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical group COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 description 1
- DGFZGSYXNZEEEW-UHFFFAOYSA-N 2-(dibutylamino)-6,8-dimethyl-3,5,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-one Chemical compound C(CCC)N(C=1N=C(C2=C(N=1)C(CN(C2)C)C)O)CCCC DGFZGSYXNZEEEW-UHFFFAOYSA-N 0.000 description 1
- MQVWDWIJODBFFR-UHFFFAOYSA-N 2-benzyl-6,8-dimethyl-3,5,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-one Chemical compound C(C1=CC=CC=C1)C=1N=C(C2=C(N=1)C(CN(C2)C)C)O MQVWDWIJODBFFR-UHFFFAOYSA-N 0.000 description 1
- UBSBLGBWNYUPDW-UHFFFAOYSA-N 2-phenylethanimidamide;hydrochloride Chemical compound Cl.NC(=N)CC1=CC=CC=C1 UBSBLGBWNYUPDW-UHFFFAOYSA-N 0.000 description 1
- TXPKUUXHNFRBPS-UHFFFAOYSA-N 3-(2-carboxyethylamino)propanoic acid Chemical class OC(=O)CCNCCC(O)=O TXPKUUXHNFRBPS-UHFFFAOYSA-N 0.000 description 1
- XYYZKOFIMYHHAG-UHFFFAOYSA-N 5,6,7,8-tetrahydro-1h-pyrido[4,3-d]pyrimidin-4-one Chemical compound C1CNCC2=C1NC=NC2=O XYYZKOFIMYHHAG-UHFFFAOYSA-N 0.000 description 1
- ZFDAAWJEBQLIFC-UHFFFAOYSA-N 6,8-dimethyl-2-methylsulfanyl-1,5,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-one Chemical compound C1N(C)CC(C)C2=C1C(=O)N=C(SC)N2 ZFDAAWJEBQLIFC-UHFFFAOYSA-N 0.000 description 1
- FQOUXHMCRLPMLW-UHFFFAOYSA-N 6-butyl-2-(hexylamino)-3,5,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-one Chemical compound C(CCCCC)NC=1N=C(C2=C(N=1)CCN(C2)CCCC)O FQOUXHMCRLPMLW-UHFFFAOYSA-N 0.000 description 1
- SQLRCGLEZSYJCK-UHFFFAOYSA-N 6-butyl-2-methylsulfanyl-1,5,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-one Chemical compound N1C(SC)=NC(=O)C2=C1CCN(CCCC)C2 SQLRCGLEZSYJCK-UHFFFAOYSA-N 0.000 description 1
- YYQPOLGVPXEPAG-UHFFFAOYSA-N CN(C=1N=C(C2=C(N=1)CCN(C2)C)O)C Chemical compound CN(C=1N=C(C2=C(N=1)CCN(C2)C)O)C YYQPOLGVPXEPAG-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 101000874159 Mus musculus Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Proteins 0.000 description 1
- DJEQZVQFEPKLOY-UHFFFAOYSA-N N,N-dimethylbutylamine Chemical compound CCCCN(C)C DJEQZVQFEPKLOY-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 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
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000006487 butyl benzyl group Chemical group 0.000 description 1
- UTOVMEACOLCUCK-PLNGDYQASA-N butyl maleate Chemical compound CCCCOC(=O)\C=C/C(O)=O UTOVMEACOLCUCK-PLNGDYQASA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- 230000000916 dilatatory effect Effects 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- GDHRQDYGUDOEIZ-UHFFFAOYSA-N n,n,2-trimethylpropan-1-amine Chemical compound CC(C)CN(C)C GDHRQDYGUDOEIZ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
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
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA764962A CA764962A (en) | 1962-03-22 | Pyrido-pyrimidines | |
| DET21812A DE1285478B (de) | 1962-03-22 | 1962-03-22 | Verfahren zur Herstellung von neuen 5, 6, 7, 8-Tetrahydropyrido-[4, 3-d]pyrimidinen |
| CH302863A CH435305A (de) | 1962-03-22 | 1963-03-11 | Verfahren zur Herstellung von neuen 5,6,7,8-Tetrahydropyrido (4,3-d)pyrimidinen |
| US265051A US3306901A (en) | 1962-03-22 | 1963-03-14 | 4-hydroxy-5,6,7,8-tetrahydro-pyrido-[4,3-d]-pyrimidine substitution products |
| GB10640/63A GB1033383A (en) | 1962-03-22 | 1963-03-18 | New tetrahydro-pyrido-[4,3-d]-pyrimidines |
| FR928686A FR2928M (enExample) | 1962-03-22 | 1963-03-20 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET21812A DE1285478B (de) | 1962-03-22 | 1962-03-22 | Verfahren zur Herstellung von neuen 5, 6, 7, 8-Tetrahydropyrido-[4, 3-d]pyrimidinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1285478B true DE1285478B (de) | 1968-12-19 |
Family
ID=7550279
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DET21812A Pending DE1285478B (de) | 1962-03-22 | 1962-03-22 | Verfahren zur Herstellung von neuen 5, 6, 7, 8-Tetrahydropyrido-[4, 3-d]pyrimidinen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3306901A (enExample) |
| CA (1) | CA764962A (enExample) |
| CH (1) | CH435305A (enExample) |
| DE (1) | DE1285478B (enExample) |
| FR (1) | FR2928M (enExample) |
| GB (1) | GB1033383A (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3444168A (en) * | 1966-12-30 | 1969-05-13 | Sterling Drug Inc | 6 - (lower-alkanoyl) - 4 - hydroxy - 2 - mercapto - 5,6,7,8 - tetrahydropyrido(4,3 - d)pyrimidines |
| US3725405A (en) * | 1970-06-18 | 1973-04-03 | American Home Prod | 2,4,7-TRISUBSTITUTED-{8 PYRIDO 2,3-d{9 PYRIMIDINE-6-CARBOXAMIDES |
| DE3729657A1 (de) * | 1987-09-04 | 1989-03-23 | Hoechst Ag | Harzsaeureester auf basis von novolakoxalkylaten, ihre herstellung und verwendung |
| DE3822043A1 (de) * | 1988-06-30 | 1990-01-11 | Hoechst Ag | Grenzflaechenaktive verbindungen auf basis von oxynaphthoesaeureestern, ihre herstellung und verwendung |
| US5212310A (en) * | 1991-12-19 | 1993-05-18 | Neurogen Corporation | Certain aryl fused imidazopyrimidines; a new class of GABA brain receptor ligands |
| EP1607396A1 (en) * | 1999-12-17 | 2005-12-21 | Chiron Corporation | Bicyclic inhibitors of glycogen synthase kinase 3 |
| WO2001044246A1 (en) * | 1999-12-17 | 2001-06-21 | Chiron Corporation | Bicyclic inhibitors of glycogen synthase kinase 3 |
| PA8539401A1 (es) * | 2001-02-14 | 2002-10-28 | Warner Lambert Co | Quinazolinas como inhibidores de mmp-13 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2802826A (en) * | 1955-07-13 | 1957-08-13 | Hoffmann La Roche | Octahydro-pyrido [4, 3-d] pyrimidine compounds |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2697710A (en) * | 1953-01-02 | 1954-12-21 | Burroughs Wellcome Co | Pyrido (2,3-d) pyrimidines and method of preparing same |
| US2926166A (en) * | 1954-01-04 | 1960-02-23 | Burroughs Wellcome Co | Pyrido (2, 3-d) pyrimidine compounds and method of making |
| US2890152A (en) * | 1956-11-29 | 1959-06-09 | Schering Corp | Topical anti-inflammatory compositions |
| US2994640A (en) * | 1957-02-22 | 1961-08-01 | Byk Gulden Lomberg Chem Fab | Anti-inflammatory therapy with purine molecular compounds |
| US3149106A (en) * | 1962-02-23 | 1964-09-15 | Smith Kline French Lab | Method of preparation of heterocyclic compounds |
-
0
- CA CA764962A patent/CA764962A/en not_active Expired
-
1962
- 1962-03-22 DE DET21812A patent/DE1285478B/de active Pending
-
1963
- 1963-03-11 CH CH302863A patent/CH435305A/de unknown
- 1963-03-14 US US265051A patent/US3306901A/en not_active Expired - Lifetime
- 1963-03-18 GB GB10640/63A patent/GB1033383A/en not_active Expired
- 1963-03-20 FR FR928686A patent/FR2928M/fr not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2802826A (en) * | 1955-07-13 | 1957-08-13 | Hoffmann La Roche | Octahydro-pyrido [4, 3-d] pyrimidine compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| CH435305A (de) | 1967-05-15 |
| GB1033383A (en) | 1966-06-22 |
| CA764962A (en) | 1967-08-08 |
| FR2928M (enExample) | 1964-12-18 |
| US3306901A (en) | 1967-02-28 |
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