DD229990A5 - Verfahren zur herstellung von neuen 2-piperazino-pteridine - Google Patents

Verfahren zur herstellung von neuen 2-piperazino-pteridine Download PDF

Info

Publication number: DD229990A5
Authority: DD; German Democratic Republic
Prior art keywords: pteridine; piperazino; group; morpholino; oxidothiomorpholino
Prior art date: 1983-07-02

Application number

DD84264739A

Other languages

German (de)

English (en)

Inventor

Josef Roch

Josef Nickl

Erich Mueller

Berthold Narr

Rainer Zimmermann

Johannes Weissenberger

Walter Haarmann

Original Assignee

Thomae Gmbh Dr K

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.)

1983-07-02

Filing date

1984-06-29

Publication date

1985-11-20

1984-06-29 Application filed by Thomae Gmbh Dr K filed Critical Thomae Gmbh Dr K

1985-11-20 Publication of DD229990A5 publication Critical patent/DD229990A5/de

Links

RIBWUHCWCPYSQW-UHFFFAOYSA-N 2-piperazin-1-ylpteridine Chemical compound C1CNCCN1C1=NC=C(N=CC=N2)C2=N1 RIBWUHCWCPYSQW-UHFFFAOYSA-N 0.000 title claims abstract description 7
238000004519 manufacturing process Methods 0.000 title description 11
-1 piperidino, morpholino, thiomorpholino Chemical group 0.000 claims abstract description 38
150000001875 compounds Chemical class 0.000 claims abstract description 26
150000003839 salts Chemical class 0.000 claims abstract description 18
238000000034 method Methods 0.000 claims abstract description 13
125000000217 alkyl group Chemical group 0.000 claims abstract description 7
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
125000005843 halogen group Chemical group 0.000 claims abstract description 7
125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 5
125000002071 phenylalkoxy group Chemical group 0.000 claims abstract description 4
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 3
125000004660 phenylalkylthio group Chemical group 0.000 claims abstract description 3
239000002253 acid Substances 0.000 claims description 19
239000002904 solvent Substances 0.000 claims description 11
150000007522 mineralic acids Chemical class 0.000 claims description 9
150000007524 organic acids Chemical class 0.000 claims description 9
235000005985 organic acids Nutrition 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 7
239000000155 melt Substances 0.000 claims description 6
238000009835 boiling Methods 0.000 claims description 4
230000001681 protective effect Effects 0.000 claims description 4
239000011230 binding agent Substances 0.000 claims description 2
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230000000144 pharmacologic effect Effects 0.000 abstract description 7
206010027476 Metastases Diseases 0.000 abstract description 6
230000002401 inhibitory effect Effects 0.000 abstract description 6
230000009401 metastasis Effects 0.000 abstract description 6
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239000003146 anticoagulant agent Substances 0.000 abstract description 5
230000008018 melting Effects 0.000 description 29
238000002844 melting Methods 0.000 description 29
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 26
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 18
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LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 7
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CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 6
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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 3
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UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 3
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UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 3
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LMVFNDSHGZYKQX-UHFFFAOYSA-N n-benzyl-6-chloro-4-(1-oxo-1,4-thiazinan-4-yl)-2-piperazin-1-ylpteridin-7-amine Chemical compound ClC1=NC2=C(N3CCS(=O)CC3)N=C(N3CCNCC3)N=C2N=C1NCC1=CC=CC=C1 LMVFNDSHGZYKQX-UHFFFAOYSA-N 0.000 description 3
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YHIIJNLSGULWAA-UHFFFAOYSA-N 1,4-thiazinane 1-oxide Chemical group O=S1CCNCC1 YHIIJNLSGULWAA-UHFFFAOYSA-N 0.000 description 2
SYMOKCJKMFKCNO-UHFFFAOYSA-N 2,4,6,7-tetrachloropteridine Chemical compound N1=C(Cl)C(Cl)=NC2=NC(Cl)=NC(Cl)=C21 SYMOKCJKMFKCNO-UHFFFAOYSA-N 0.000 description 2
WFJIEXVIJLOOAS-UHFFFAOYSA-N 2,6-dichloro-4,7-di(piperidin-1-yl)pteridine Chemical compound C=12N=C(Cl)C(N3CCCCC3)=NC2=NC(Cl)=NC=1N1CCCCC1 WFJIEXVIJLOOAS-UHFFFAOYSA-N 0.000 description 2
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RQGLYVVHIOMMAT-UHFFFAOYSA-N 4-(2,6-dichloro-4-morpholin-4-ylpteridin-7-yl)morpholine Chemical compound C=12N=C(Cl)C(N3CCOCC3)=NC2=NC(Cl)=NC=1N1CCOCC1 RQGLYVVHIOMMAT-UHFFFAOYSA-N 0.000 description 2
NUSUTTMBCGSOLF-UHFFFAOYSA-N 4-(3-piperidin-1-ylthiomorpholin-4-yl)morpholine Chemical compound N1(CCCCC1)C1N(CCSC1)N1CCOCC1 NUSUTTMBCGSOLF-UHFFFAOYSA-N 0.000 description 2
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SQEZFVLSKXCCRY-UHFFFAOYSA-N 4-n,4-n,7-n,7-n-tetramethyl-6-phenylmethoxy-2-piperazin-1-ylpteridine-4,7-diamine Chemical compound CN(C)C1=NC2=NC(N3CCNCC3)=NC(N(C)C)=C2N=C1OCC1=CC=CC=C1 SQEZFVLSKXCCRY-UHFFFAOYSA-N 0.000 description 1
UELGJSYQDBKRIP-UHFFFAOYSA-N 6-chloro-2-piperazin-1-yl-4,7-di(piperidin-1-yl)pteridine Chemical compound ClC1=NC2=C(N3CCCCC3)N=C(N3CCNCC3)N=C2N=C1N1CCCCC1 UELGJSYQDBKRIP-UHFFFAOYSA-N 0.000 description 1
KBWMIUUWZNOXTB-UHFFFAOYSA-N 6-chloro-4-n,4-n,7-n,7-n-tetramethyl-2-piperazin-1-ylpteridine-4,7-diamine Chemical group N=1C(N(C)C)=C2N=C(Cl)C(N(C)C)=NC2=NC=1N1CCNCC1 KBWMIUUWZNOXTB-UHFFFAOYSA-N 0.000 description 1
CBKKKHCLVATMNE-UHFFFAOYSA-N 7-n-benzyl-2,6-dichloro-4-n,4-n-dimethylpteridine-4,7-diamine Chemical compound ClC=1N=C2C(N(C)C)=NC(Cl)=NC2=NC=1NCC1=CC=CC=C1 CBKKKHCLVATMNE-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 description 1
208000001382 Experimental Melanoma Diseases 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
101150084935 PTER gene Proteins 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
208000001435 Thromboembolism Diseases 0.000 description 1
208000032109 Transient ischaemic attack Diseases 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
208000007957 amaurosis fugax Diseases 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000002001 anti-metastasis Effects 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
239000002221 antipyretic Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
239000002585 base Substances 0.000 description 1
235000013871 bee wax Nutrition 0.000 description 1
239000012166 beeswax Substances 0.000 description 1
235000019445 benzyl alcohol Nutrition 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
238000004364 calculation method Methods 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229940099112 cornstarch Drugs 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
230000000916 dilatatory effect Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
150000004656 dimethylamines Chemical class 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
238000011049 filling Methods 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
229960001375 lactose Drugs 0.000 description 1
238000012417 linear regression Methods 0.000 description 1
239000000314 lubricant Substances 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
206010061289 metastatic neoplasm Diseases 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
150000003956 methylamines Chemical class 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
IAFVMQYEKYMWPH-UHFFFAOYSA-N n-benzyl-2,6-dichloro-4-(1-oxo-1,4-thiazinan-4-yl)pteridin-7-amine Chemical compound C=12N=C(Cl)C(NCC=3C=CC=CC=3)=NC2=NC(Cl)=NC=1N1CCS(=O)CC1 IAFVMQYEKYMWPH-UHFFFAOYSA-N 0.000 description 1
BOALMGLHXFGVHW-UHFFFAOYSA-N n-benzyl-2,6-dichloro-4-thiomorpholin-4-ylpteridin-7-amine Chemical compound C=12N=C(Cl)C(NCC=3C=CC=CC=3)=NC2=NC(Cl)=NC=1N1CCSCC1 BOALMGLHXFGVHW-UHFFFAOYSA-N 0.000 description 1
DXNKMGSAZKFWHS-UHFFFAOYSA-N n-benzyl-6-benzylsulfanyl-4-(1-oxo-1,4-thiazinan-4-yl)-2-piperazin-1-ylpteridin-7-amine Chemical compound C1CS(=O)CCN1C(C1=N2)=NC(N3CCNCC3)=NC1=NC(NCC=1C=CC=CC=1)=C2SCC1=CC=CC=C1 DXNKMGSAZKFWHS-UHFFFAOYSA-N 0.000 description 1
OQNACIGXVSOVBH-UHFFFAOYSA-N n-benzyl-6-chloro-4-morpholin-4-yl-2-piperazin-1-ylpteridin-7-amine Chemical compound ClC1=NC2=C(N3CCOCC3)N=C(N3CCNCC3)N=C2N=C1NCC1=CC=CC=C1 OQNACIGXVSOVBH-UHFFFAOYSA-N 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940093430 polyethylene glycol 1500 Drugs 0.000 description 1
229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
150000003195 pteridines Chemical class 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000012216 screening Methods 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
238000005245 sintering Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
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 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 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
239000006228 supernatant Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
201000010875 transient cerebral ischemia Diseases 0.000 description 1
238000002604 ultrasonography Methods 0.000 description 1
ISPBABGJNLPGOY-UHFFFAOYSA-K zinc barium(2+) hydroxide sulfate Chemical compound [OH-].[Zn+2].[Ba+2].[O-]S([O-])(=O)=O ISPBABGJNLPGOY-UHFFFAOYSA-K 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- 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

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Diabetes (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pyrrole Compounds (AREA)

DD84264739A 1983-07-02 1984-06-29 Verfahren zur herstellung von neuen 2-piperazino-pteridine DD229990A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19833323932 DE3323932A1 (de)	1983-07-02	1983-07-02	Neue 2-piperazino-pteridine, verfahren zu ihrer herstellung und diese verbindung enthaltende arzneimittel

Publications (1)

Publication Number	Publication Date
DD229990A5 true DD229990A5 (de)	1985-11-20

Family

ID=6203017

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD84264739A DD229990A5 (de)	1983-07-02	1984-06-29	Verfahren zur herstellung von neuen 2-piperazino-pteridine

Country Status (17)

Country	Link
EP (1)	EP0134922B1 (da)
JP (1)	JPS6025991A (da)
AT (1)	ATE39253T1 (da)
AU (1)	AU565105B2 (da)
CA (1)	CA1233179A (da)
DD (1)	DD229990A5 (da)
DE (2)	DE3323932A1 (da)
DK (1)	DK159113C (da)
ES (2)	ES8503352A1 (da)
FI (1)	FI80454C (da)
GB (1)	GB2143232B (da)
HU (1)	HU190932B (da)
IL (1)	IL72265A (da)
NO (1)	NO160920C (da)
NZ (1)	NZ208725A (da)
PH (1)	PH22493A (da)
ZA (1)	ZA844968B (da)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3445298A1 (de) *	1984-12-12	1986-06-12	Dr. Karl Thomae Gmbh, 7950 Biberach	Neue pteridine, verfahren zu ihrer herstellung und deren verwendung als zwischenprodukte oder als arzneimittel
DE3540952C2 (de) *	1985-11-19	1997-08-14	Thomae Gmbh Dr K	2-Piperazino-pteridine, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
US7276506B2 (en)	1998-12-28	2007-10-02	4 Aza Bioscience Nv	Immunosuppressive effects of pteridine derivatives
DE10202468A1 (de) *	2002-01-23	2004-09-30	Faustus Forschungs Cie. Translational Cancer Research Gmbh	Pteridinderivate, Verfahren zu deren Herstellung und ihre Verwendung
AU2004267885A1 (en) *	2003-08-29	2005-03-10	4 Aza Bioscience Nv	Immunosuppressive effects of pteridine derivatives
GB2407089A (en) *	2003-10-17	2005-04-20	4 Aza Bioscience Nv	Pteridine derivatives
DE102004057645A1 (de) *	2004-11-29	2006-06-01	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Substituierte Pteridine zur Behandlung von entzündlichen Erkrankungen
DE102004057595A1 (de)	2004-11-29	2006-06-08	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Substituierte Pteridine zur Behandlung von entzündlichen Erkrankungen
DE102004057618A1 (de)	2004-11-29	2006-06-01	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Substituierte Pteridine zur Behandlung von entzündlichen Erkrankungen
DE102004057594A1 (de)	2004-11-29	2006-06-08	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Substitueirte Pteridine zur Behandlung von entzündlichen Erkrankungen
EP2029600B1 (de) *	2006-05-24	2012-03-14	Boehringer Ingelheim International GmbH	Substituierte pteridine, die mit einem viergliedrigen heterocyclus substituiert sind
JP5440934B2 (ja) *	2006-05-24	2014-03-12	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	置換プテリジン
WO2008003149A2 (en) *	2006-07-06	2008-01-10	Gilead Sciences , Inc.	Substituted pteridines for the treatment and prevention of viral infections
WO2008009078A2 (en)	2006-07-20	2008-01-24	Gilead Sciences, Inc.	4,6-dl- and 2,4,6-trisubstituted quinazoline derivatives useful for treating viral infections
US10144736B2 (en)	2006-07-20	2018-12-04	Gilead Sciences, Inc.	Substituted pteridines useful for the treatment and prevention of viral infections
US9670205B2 (en)	2015-03-04	2017-06-06	Gilead Sciences, Inc.	Toll like receptor modulator compounds
AU2017318601B2 (en)	2016-09-02	2020-09-03	Gilead Sciences, Inc.	Toll like receptor modulator compounds
WO2018045150A1 (en)	2016-09-02	2018-03-08	Gilead Sciences, Inc.	4,6-diamino-pyrido[3,2-d]pyrimidine derivaties as toll like receptor modulators
TWI751516B (zh)	2019-04-17	2022-01-01	美商基利科學股份有限公司	類鐸受體調節劑之固體形式
TW202212339A (zh)	2019-04-17	2022-04-01	美商基利科學股份有限公司	類鐸受體調節劑之固體形式
TWI879779B (zh)	2019-06-28	2025-04-11	美商基利科學股份有限公司	類鐸受體調節劑化合物的製備方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2940972A (en) *	1957-06-27	1960-06-14	Thomae Gmbh Dr K	Tri-and tetra-substituted pteridine derivatives
FR1352111A (fr) *	1962-01-25	1964-02-14	Lumiere Lab	Triamino ptéridines et leur préparation

1983
- 1983-07-02 DE DE19833323932 patent/DE3323932A1/de not_active Withdrawn
1984
- 1984-06-11 ES ES533298A patent/ES8503352A1/es not_active Expired
- 1984-06-19 AT AT84106993T patent/ATE39253T1/de not_active IP Right Cessation
- 1984-06-19 DE DE8484106993T patent/DE3475620D1/de not_active Expired
- 1984-06-19 EP EP84106993A patent/EP0134922B1/de not_active Expired
- 1984-06-28 DK DK316284A patent/DK159113C/da not_active IP Right Cessation
- 1984-06-28 JP JP59132187A patent/JPS6025991A/ja active Pending
- 1984-06-29 GB GB08416682A patent/GB2143232B/en not_active Expired
- 1984-06-29 IL IL72265A patent/IL72265A/xx unknown
- 1984-06-29 CA CA000457880A patent/CA1233179A/en not_active Expired
- 1984-06-29 ZA ZA844968A patent/ZA844968B/xx unknown
- 1984-06-29 DD DD84264739A patent/DD229990A5/de not_active IP Right Cessation
- 1984-06-29 PH PH30906A patent/PH22493A/en unknown
- 1984-06-29 NZ NZ208725A patent/NZ208725A/xx unknown
- 1984-06-29 NO NO842631A patent/NO160920C/no unknown
- 1984-06-29 FI FI842622A patent/FI80454C/fi not_active IP Right Cessation
- 1984-07-02 AU AU30092/84A patent/AU565105B2/en not_active Ceased
- 1984-07-02 HU HU842559A patent/HU190932B/hu not_active IP Right Cessation
- 1984-11-20 ES ES537785A patent/ES8601205A1/es not_active Expired

Also Published As

Publication number	Publication date
GB8416682D0 (en)	1984-08-01
NZ208725A (en)	1988-10-28
IL72265A0 (en)	1984-10-31
DK159113C (da)	1991-02-18
PH22493A (en)	1988-09-12
ES533298A0 (es)	1985-02-16
ZA844968B (en)	1986-03-26
DE3475620D1 (en)	1989-01-19
FI80454B (fi)	1990-02-28
DE3323932A1 (de)	1985-01-10
DK316284D0 (da)	1984-06-28
CA1233179A (en)	1988-02-23
HUT34487A (en)	1985-03-28
NO842631L (no)	1985-01-03
AU3009284A (en)	1985-01-03
JPS6025991A (ja)	1985-02-08
ES8503352A1 (es)	1985-02-16
FI80454C (fi)	1990-06-11
GB2143232A (en)	1985-02-06
EP0134922B1 (de)	1988-12-14
IL72265A (en)	1987-08-31
HU190932B (en)	1986-12-28
DK316284A (da)	1985-01-03
FI842622A7 (fi)	1985-01-03
DK159113B (da)	1990-09-03
ATE39253T1 (de)	1988-12-15
AU565105B2 (en)	1987-09-03
ES537785A0 (es)	1985-10-16
NO160920C (no)	1989-06-14
FI842622A0 (fi)	1984-06-29
GB2143232B (en)	1986-11-05
EP0134922A1 (de)	1985-03-27
NO160920B (no)	1989-03-06
ES8601205A1 (es)	1985-10-16

Legal Events

Date	Code	Title	Description
1995-09-14	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD229990A5 (de)	1985-11-20	Verfahren zur herstellung von neuen 2-piperazino-pteridine
EP1427730B1 (de)	2006-07-12	Neue dihydropteridinone, verfahren zu deren herstellung und deren verwendung als arzneimittel
DE3445298A1 (de)	1986-06-12	Neue pteridine, verfahren zu ihrer herstellung und deren verwendung als zwischenprodukte oder als arzneimittel
EP1761536B1 (de)	2007-12-26	Neue 2-benzylaminodihydropteridinone, verfahren zu deren herstellung und deren verwendung als arzneimittel
EP1216246B1 (de)	2005-08-24	N-substituierte 4-aminopteridine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
DE10057751A1 (de)	2002-05-23	Neue Carbamat-substituierte Pyrazolopyridinderivate
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