FI80454B - Foerfarande foer framstaellning av farmakologiskt vaerdefulla 2-piperazino-pteridiner. - Google Patents
Foerfarande foer framstaellning av farmakologiskt vaerdefulla 2-piperazino-pteridiner. Download PDFInfo
- Publication number
- FI80454B FI80454B FI842622A FI842622A FI80454B FI 80454 B FI80454 B FI 80454B FI 842622 A FI842622 A FI 842622A FI 842622 A FI842622 A FI 842622A FI 80454 B FI80454 B FI 80454B
- Authority
- FI
- Finland
- Prior art keywords
- piperazino
- group
- pteridine
- acid addition
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims description 9
- 230000000144 pharmacologic effect Effects 0.000 title abstract description 6
- -1 piperidino, morpholino, thiomorpholino Chemical group 0.000 claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 239000002253 acid Substances 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- RIBWUHCWCPYSQW-UHFFFAOYSA-N 2-piperazin-1-ylpteridine Chemical class C1CNCCN1C1=NC=C(N=CC=N2)C2=N1 RIBWUHCWCPYSQW-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 6
- 125000002071 phenylalkoxy group Chemical group 0.000 claims abstract description 5
- 125000004660 phenylalkylthio group Chemical group 0.000 claims abstract description 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 26
- 150000007522 mineralic acids Chemical class 0.000 claims description 8
- 150000007524 organic acids Chemical class 0.000 claims description 8
- 235000005985 organic acids Nutrition 0.000 claims description 7
- KBWMIUUWZNOXTB-UHFFFAOYSA-N 6-chloro-4-n,4-n,7-n,7-n-tetramethyl-2-piperazin-1-ylpteridine-4,7-diamine Chemical compound N=1C(N(C)C)=C2N=C(Cl)C(N(C)C)=NC2=NC=1N1CCNCC1 KBWMIUUWZNOXTB-UHFFFAOYSA-N 0.000 claims description 4
- FFICMHCVZYLUGN-UHFFFAOYSA-N 6-benzylsulfanyl-4-n,4-n,7-n,7-n-tetramethyl-2-piperazin-1-ylpteridine-4,7-diamine Chemical compound CN(C)C1=NC2=NC(N3CCNCC3)=NC(N(C)C)=C2N=C1SCC1=CC=CC=C1 FFICMHCVZYLUGN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001447 alkali salts Chemical class 0.000 claims description 3
- XRDQMYPAAREORR-UHFFFAOYSA-N 4-(6-benzylsulfanyl-4-morpholin-4-yl-2-piperazin-1-ylpteridin-7-yl)morpholine Chemical compound C=1C=CC=CC=1CSC1=NC2=C(N3CCOCC3)N=C(N3CCNCC3)N=C2N=C1N1CCOCC1 XRDQMYPAAREORR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
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- 230000002401 inhibitory effect Effects 0.000 abstract description 8
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- 208000001435 Thromboembolism Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 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
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000011230 binding agent Substances 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
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 229960000956 coumarin 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
- 238000004821 distillation Methods 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940116364 hard fat Drugs 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 230000001394 metastastic effect Effects 0.000 description 1
- 206010061289 metastatic neoplasm Diseases 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- YIIAUNGSHVNRFT-UHFFFAOYSA-N n-benzyl-2,6-dichloro-4-morpholin-4-ylpteridin-7-amine Chemical compound C=12N=C(Cl)C(NCC=3C=CC=CC=3)=NC2=NC(Cl)=NC=1N1CCOCC1 YIIAUNGSHVNRFT-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
- VMXWLOTXSJWQPN-UHFFFAOYSA-N n-benzyl-6-methoxy-4-(1-oxo-1,4-thiazinan-4-yl)-2-piperazin-1-ylpteridin-7-amine Chemical compound COC1=NC2=C(N3CCS(=O)CC3)N=C(N3CCNCC3)N=C2N=C1NCC1=CC=CC=C1 VMXWLOTXSJWQPN-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone 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
- 239000000843 powder Substances 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
- 239000003380 propellant Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 150000003195 pteridines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000003826 tablet 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
- 210000004881 tumor cell Anatomy 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (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)
Claims (4)
1. Förfarande för framställning av farmakologiskt värdefulla 2-piperazinopteridiner med formeln I R1 N N N N- H (I) R2 där Rl är fenyläiky1amino-» dialkylaminogrupp, piperidino-, morfo-lino-, tiomorfolino- eller 1-oxidotiomorfolinogrupp, R2 är dialkylamino-, piperidino-, morfolino-, tiomorfolino-eller 1-oxidotiomorfolinogrupp och R3 är halogenatom, alkoxi-alkyltio-, fenylalkoxi- eller fenylalkyltiogrupp, varvid alkyldelen i respektive fall kan innehalla 1-3 kolatomer, och deras syraadditionssalter, speciellt deras fysiologiskt lampiiga syraadditionssalter med oorganiska eller organiska syror, kännetecknat därav, att a) för framställning av föreningar med den allmänna formeln I, där R3 är en halogenatom, bringas en förening med den allmänna formeln II Rlx^NYN^Z2 I an Rt A n R2 där Rl och R2 avser samma som ovan, 23 80454 R'3 är halogenatom och Z2 är en nukleofiliskt utbytbar grupp, sasom en halogenatom, att reagera med et piperazin med den allmänna formeln II H - N N - H (III) eller b) för framställning av föreningar med den allmänna formeln I, där R3 är alkoxi-, alkylmerkapto-, fenylalkoxi- eller fenyl-alkylmerkaptogrupp, brlngas en förening med den allmänna formeln IV R, . ^ N Nv /N N- H Ύ Y z3^n *2 där R^ och R2 avser samma som ovan och Z3 är en nukloefiliskt utbytbar grupp, sasom en halogenatom, att reagera med en förening med den allmänna formeln V R31 - H (V) där R31 eventuellt är en med fenylgrupp substituerad alkoxi- eller alkylmerkaptogrupp, varvid alkyldelen respektive innehaller 1-3 kolatomer, eller omsättes med dennas aikaiisalt och därefter vid behov överföres en sl erhallen förening med den 24 80454 allmänna formeln I till sitt syraadditionssalt, speciellt till sitt fysiologiskt lämpliga syraadditionssalt med en oorganisk eller organisk syra.
2. Förfarande enligt patentkravet 1, kännetecknat därav, att den framställda föreningen med formeln I Mr 6-bensyltio-4,7-dimorfolino-2-piperazino-pteridin eller dess syraadditionssalt.
3. Förfarande enligt patentkravet 1, kännetecknat därav, att den framställda föreningen med formeln i Mr 6-klor- 4,7-bis-(dimetylamino)-2-piperazino-pteridin eller dess syraadditionssalt.
4. Förfarande enligt patentkravet 1, kännetecknat därav, att den framställda föreningen med formeln I Mr 6-bensyltio-4,7-bis-(dimetylamino)-2-piperazino-pteridin eller dess syraadditionssalt. i!
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3323932 | 1983-07-02 | ||
| DE19833323932 DE3323932A1 (de) | 1983-07-02 | 1983-07-02 | Neue 2-piperazino-pteridine, verfahren zu ihrer herstellung und diese verbindung enthaltende arzneimittel |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI842622A0 FI842622A0 (fi) | 1984-06-29 |
| FI842622A7 FI842622A7 (fi) | 1985-01-03 |
| FI80454B true FI80454B (fi) | 1990-02-28 |
| FI80454C FI80454C (sv) | 1990-06-11 |
Family
ID=6203017
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI842622A FI80454C (sv) | 1983-07-02 | 1984-06-29 | Förfarande för framställning av farmakologiskt värdefulla 2-piperazino -pteridiner |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0134922B1 (sv) |
| JP (1) | JPS6025991A (sv) |
| AT (1) | ATE39253T1 (sv) |
| AU (1) | AU565105B2 (sv) |
| CA (1) | CA1233179A (sv) |
| DD (1) | DD229990A5 (sv) |
| DE (2) | DE3323932A1 (sv) |
| DK (1) | DK159113C (sv) |
| ES (2) | ES8503352A1 (sv) |
| FI (1) | FI80454C (sv) |
| GB (1) | GB2143232B (sv) |
| HU (1) | HU190932B (sv) |
| IL (1) | IL72265A (sv) |
| NO (1) | NO160920C (sv) |
| NZ (1) | NZ208725A (sv) |
| PH (1) | PH22493A (sv) |
| ZA (1) | ZA844968B (sv) |
Families Citing this family (21)
| 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 |
| ES2295897T3 (es) * | 2003-08-29 | 2008-04-16 | 4 Aza Ip Nv | Efectos inmunodepresores de derivados de pteridina. |
| GB2407089A (en) * | 2003-10-17 | 2005-04-20 | 4 Aza Bioscience Nv | Pteridine derivatives |
| DE102004057595A1 (de) | 2004-11-29 | 2006-06-08 | 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 |
| DE102004057618A1 (de) * | 2004-11-29 | 2006-06-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Substituierte Pteridine zur Behandlung von entzündlichen Erkrankungen |
| DE102004057645A1 (de) * | 2004-11-29 | 2006-06-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Substituierte Pteridine zur Behandlung von entzündlichen Erkrankungen |
| US20100234347A1 (en) * | 2006-05-24 | 2010-09-16 | Boehringer Ingelheim Internationl Gmbh | Substituted Pteridines substituted with a Four-Membered Heterocycle |
| EP2032585B1 (de) | 2006-05-24 | 2014-07-23 | Boehringer Ingelheim International GmbH | Substituierte pteridine als therapeutika |
| WO2008003149A2 (en) * | 2006-07-06 | 2008-01-10 | Gilead Sciences , Inc. | Substituted pteridines for the treatment and prevention of viral infections |
| WO2008009079A2 (en) | 2006-07-20 | 2008-01-24 | Gilead Sciences, Inc. | Substituted pteridines useful 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 |
| PH12021551982A1 (en) | 2015-03-04 | 2022-09-05 | Gilead Sciences Inc | Toll-like receptor modulating 4,6-diamino-pyrido[3,2-d]pyrimidine compounds |
| US10640499B2 (en) | 2016-09-02 | 2020-05-05 | Gilead Sciences, Inc. | Toll like receptor modulator compounds |
| US10370342B2 (en) | 2016-09-02 | 2019-08-06 | Gilead Sciences, Inc. | Toll like receptor modulator compounds |
| TWI751517B (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 |
| TW202210480A (zh) | 2019-04-17 | 2022-03-16 | 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)
| 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 DE DE8484106993T patent/DE3475620D1/de not_active Expired
- 1984-06-19 AT AT84106993T patent/ATE39253T1/de not_active IP Right Cessation
- 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 NO NO842631A patent/NO160920C/no unknown
- 1984-06-29 DD DD84264739A patent/DD229990A5/de not_active IP Right Cessation
- 1984-06-29 GB GB08416682A patent/GB2143232B/en not_active Expired
- 1984-06-29 FI FI842622A patent/FI80454C/sv not_active IP Right Cessation
- 1984-06-29 CA CA000457880A patent/CA1233179A/en not_active Expired
- 1984-06-29 NZ NZ208725A patent/NZ208725A/xx unknown
- 1984-06-29 ZA ZA844968A patent/ZA844968B/xx unknown
- 1984-06-29 PH PH30906A patent/PH22493A/en unknown
- 1984-06-29 IL IL72265A patent/IL72265A/xx unknown
- 1984-07-02 HU HU842559A patent/HU190932B/hu not_active IP Right Cessation
- 1984-07-02 AU AU30092/84A patent/AU565105B2/en not_active Ceased
- 1984-11-20 ES ES537785A patent/ES8601205A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB2143232A (en) | 1985-02-06 |
| DK316284A (da) | 1985-01-03 |
| GB2143232B (en) | 1986-11-05 |
| CA1233179A (en) | 1988-02-23 |
| EP0134922B1 (de) | 1988-12-14 |
| DK316284D0 (da) | 1984-06-28 |
| AU3009284A (en) | 1985-01-03 |
| ES537785A0 (es) | 1985-10-16 |
| FI842622A7 (fi) | 1985-01-03 |
| ES8601205A1 (es) | 1985-10-16 |
| HU190932B (en) | 1986-12-28 |
| NO160920B (no) | 1989-03-06 |
| DK159113B (da) | 1990-09-03 |
| DK159113C (da) | 1991-02-18 |
| ES533298A0 (es) | 1985-02-16 |
| NO160920C (no) | 1989-06-14 |
| DE3475620D1 (en) | 1989-01-19 |
| FI80454C (sv) | 1990-06-11 |
| EP0134922A1 (de) | 1985-03-27 |
| JPS6025991A (ja) | 1985-02-08 |
| NZ208725A (en) | 1988-10-28 |
| IL72265A (en) | 1987-08-31 |
| IL72265A0 (en) | 1984-10-31 |
| PH22493A (en) | 1988-09-12 |
| ZA844968B (en) | 1986-03-26 |
| DE3323932A1 (de) | 1985-01-10 |
| ATE39253T1 (de) | 1988-12-15 |
| HUT34487A (en) | 1985-03-28 |
| FI842622A0 (fi) | 1984-06-29 |
| ES8503352A1 (es) | 1985-02-16 |
| DD229990A5 (de) | 1985-11-20 |
| NO842631L (no) | 1985-01-03 |
| GB8416682D0 (en) | 1984-08-01 |
| AU565105B2 (en) | 1987-09-03 |
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