FI77454C - Foerfarande foer framstaellning av som laekemedel anvaendbara 4-anilino-pyrimidinderivat. - Google Patents
Foerfarande foer framstaellning av som laekemedel anvaendbara 4-anilino-pyrimidinderivat. Download PDFInfo
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- FI77454C FI77454C FI821990A FI821990A FI77454C FI 77454 C FI77454 C FI 77454C FI 821990 A FI821990 A FI 821990A FI 821990 A FI821990 A FI 821990A FI 77454 C FI77454 C FI 77454C
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- Finland
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- 150000001875 compounds Chemical class 0.000 claims description 74
- -1 methylenedioxy Chemical group 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 150000005694 halopyrimidines Chemical class 0.000 claims description 8
- 239000012458 free base Substances 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- JLVLBDODYLEYOY-UHFFFAOYSA-N n-phenylpyrimidin-4-amine Chemical class C=1C=NC=NC=1NC1=CC=CC=C1 JLVLBDODYLEYOY-UHFFFAOYSA-N 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000004970 halomethyl group Chemical group 0.000 claims description 2
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- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
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- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 6
- MJRSZADMKJVGQV-UHFFFAOYSA-N 4-chloro-5,6-dimethylpyrimidine Chemical compound CC1=NC=NC(Cl)=C1C MJRSZADMKJVGQV-UHFFFAOYSA-N 0.000 description 5
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- 238000010171 animal model Methods 0.000 description 3
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- 210000000744 eyelid Anatomy 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
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- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 3
- ZSYMMFVIWDNMBR-UHFFFAOYSA-N 4-[(5,6-dimethylpyrimidin-4-yl)amino]benzoic acid Chemical compound CC1=NC=NC(NC=2C=CC(=CC=2)C(O)=O)=C1C ZSYMMFVIWDNMBR-UHFFFAOYSA-N 0.000 description 2
- KTVGSASGRMITEZ-UHFFFAOYSA-N 5,6-dimethyl-n-(4-propan-2-ylphenyl)pyrimidin-4-amine Chemical compound C1=CC(C(C)C)=CC=C1NC1=NC=NC(C)=C1C KTVGSASGRMITEZ-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
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- IQTJGMBZJLOLGA-UHFFFAOYSA-N n-(2-ethoxyphenyl)-5,6-dimethylpyrimidin-4-amine Chemical compound CCOC1=CC=CC=C1NC1=NC=NC(C)=C1C IQTJGMBZJLOLGA-UHFFFAOYSA-N 0.000 description 1
- QOUVHDZWPUJUNJ-UHFFFAOYSA-N n-(2-fluorophenyl)-5,6-dimethylpyrimidin-4-amine Chemical compound CC1=NC=NC(NC=2C(=CC=CC=2)F)=C1C QOUVHDZWPUJUNJ-UHFFFAOYSA-N 0.000 description 1
- HZILDDLWZBNSCY-UHFFFAOYSA-N n-(2-methoxyphenyl)-5,6-dimethylpyrimidin-4-amine Chemical compound COC1=CC=CC=C1NC1=NC=NC(C)=C1C HZILDDLWZBNSCY-UHFFFAOYSA-N 0.000 description 1
- CMVIBVSMAWEAGX-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-5,6-dimethylpyrimidin-4-amine Chemical compound CC1=NC=NC(NC=2C=C(Cl)C(Cl)=CC=2)=C1C CMVIBVSMAWEAGX-UHFFFAOYSA-N 0.000 description 1
- DAKCFTISEKVVFI-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-5,6-dimethylpyrimidin-4-amine Chemical compound CC1=NC=NC(NC=2C=C(Cl)C=C(Cl)C=2)=C1C DAKCFTISEKVVFI-UHFFFAOYSA-N 0.000 description 1
- FZFLAEVGQMTLRD-UHFFFAOYSA-N n-(3-bromophenyl)-5,6-dimethylpyrimidin-4-amine Chemical compound CC1=NC=NC(NC=2C=C(Br)C=CC=2)=C1C FZFLAEVGQMTLRD-UHFFFAOYSA-N 0.000 description 1
- LQNZJASXDFBFSV-UHFFFAOYSA-N n-(3-chlorophenyl)-5,6-dimethylpyrimidin-4-amine Chemical compound CC1=NC=NC(NC=2C=C(Cl)C=CC=2)=C1C LQNZJASXDFBFSV-UHFFFAOYSA-N 0.000 description 1
- PVFMGYLMGCECRH-UHFFFAOYSA-N n-(3-ethoxyphenyl)-5,6-dimethylpyrimidin-4-amine Chemical compound CCOC1=CC=CC(NC=2C(=C(C)N=CN=2)C)=C1 PVFMGYLMGCECRH-UHFFFAOYSA-N 0.000 description 1
- LSEPRLDRIDLGKV-UHFFFAOYSA-N n-(3-fluorophenyl)-5,6-dimethylpyrimidin-4-amine Chemical compound CC1=NC=NC(NC=2C=C(F)C=CC=2)=C1C LSEPRLDRIDLGKV-UHFFFAOYSA-N 0.000 description 1
- HIYAQFPJGGERIU-UHFFFAOYSA-N n-(3-methoxyphenyl)-5,6-dimethylpyrimidin-4-amine Chemical compound COC1=CC=CC(NC=2C(=C(C)N=CN=2)C)=C1 HIYAQFPJGGERIU-UHFFFAOYSA-N 0.000 description 1
- APPRIARTDKIYAM-UHFFFAOYSA-N n-(4-bromophenyl)-5,6-diethylpyrimidin-4-amine Chemical compound CCC1=NC=NC(NC=2C=CC(Br)=CC=2)=C1CC APPRIARTDKIYAM-UHFFFAOYSA-N 0.000 description 1
- BPDCKJAIGZLYGO-UHFFFAOYSA-N n-(4-bromophenyl)-5,6-diethylpyrimidin-4-amine;hydrochloride Chemical compound Cl.CCC1=NC=NC(NC=2C=CC(Br)=CC=2)=C1CC BPDCKJAIGZLYGO-UHFFFAOYSA-N 0.000 description 1
- QOUKYDBYXKZUDH-UHFFFAOYSA-N n-(4-bromophenyl)-5,6-dimethylpyrimidin-4-amine Chemical compound CC1=NC=NC(NC=2C=CC(Br)=CC=2)=C1C QOUKYDBYXKZUDH-UHFFFAOYSA-N 0.000 description 1
- BTAFMBXLDMPSSE-UHFFFAOYSA-N n-(4-bromophenyl)-5-butyl-6-methylpyrimidin-4-amine Chemical compound CCCCC1=C(C)N=CN=C1NC1=CC=C(Br)C=C1 BTAFMBXLDMPSSE-UHFFFAOYSA-N 0.000 description 1
- QUJSCZFYHUQMJS-UHFFFAOYSA-N n-(4-bromophenyl)-5-ethyl-6-methylpyrimidin-4-amine Chemical compound CCC1=C(C)N=CN=C1NC1=CC=C(Br)C=C1 QUJSCZFYHUQMJS-UHFFFAOYSA-N 0.000 description 1
- REAIRYGSJJQATQ-UHFFFAOYSA-N n-(4-bromophenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound C1=CC(Br)=CC=C1NC1=NC=NC2=C1CCC2 REAIRYGSJJQATQ-UHFFFAOYSA-N 0.000 description 1
- JMEAJKDLIRMWRG-UHFFFAOYSA-N n-(4-butylphenyl)-5,6-dimethylpyrimidin-4-amine Chemical compound C1=CC(CCCC)=CC=C1NC1=NC=NC(C)=C1C JMEAJKDLIRMWRG-UHFFFAOYSA-N 0.000 description 1
- FUFNNRNORCPEPB-UHFFFAOYSA-N n-(4-chlorophenyl)-5-ethyl-6-methylpyrimidin-4-amine Chemical compound CCC1=C(C)N=CN=C1NC1=CC=C(Cl)C=C1 FUFNNRNORCPEPB-UHFFFAOYSA-N 0.000 description 1
- HKGPVGTXBOEKAC-UHFFFAOYSA-N n-(4-chlorophenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound C1=CC(Cl)=CC=C1NC1=NC=NC2=C1CCC2 HKGPVGTXBOEKAC-UHFFFAOYSA-N 0.000 description 1
- JIOFXQHOYWOYMF-UHFFFAOYSA-N n-(4-chlorophenyl)-n,5,6-trimethylpyrimidin-4-amine Chemical compound N=1C=NC(C)=C(C)C=1N(C)C1=CC=C(Cl)C=C1 JIOFXQHOYWOYMF-UHFFFAOYSA-N 0.000 description 1
- SALASVUWAZUBOH-UHFFFAOYSA-N n-(4-ethoxyphenyl)-5,6-dimethylpyrimidin-4-amine Chemical compound C1=CC(OCC)=CC=C1NC1=NC=NC(C)=C1C SALASVUWAZUBOH-UHFFFAOYSA-N 0.000 description 1
- BDBWHLYMVVYKQO-UHFFFAOYSA-N n-(4-ethoxyphenyl)-5-ethyl-6-methylpyrimidin-4-amine Chemical compound C1=CC(OCC)=CC=C1NC1=NC=NC(C)=C1CC BDBWHLYMVVYKQO-UHFFFAOYSA-N 0.000 description 1
- ODQUKYYMPYEPRD-UHFFFAOYSA-N n-(4-ethylphenyl)-5,6-dimethylpyrimidin-4-amine Chemical compound C1=CC(CC)=CC=C1NC1=NC=NC(C)=C1C ODQUKYYMPYEPRD-UHFFFAOYSA-N 0.000 description 1
- KLVPZUGZEXCQNU-UHFFFAOYSA-N n-(4-ethylphenyl)-n,5,6-trimethylpyrimidin-4-amine Chemical compound C1=CC(CC)=CC=C1N(C)C1=NC=NC(C)=C1C KLVPZUGZEXCQNU-UHFFFAOYSA-N 0.000 description 1
- WSUCXABYUTZFDX-UHFFFAOYSA-N n-(4-fluorophenyl)-5,6-dimethylpyrimidin-4-amine Chemical compound CC1=NC=NC(NC=2C=CC(F)=CC=2)=C1C WSUCXABYUTZFDX-UHFFFAOYSA-N 0.000 description 1
- OZZPXKTXAWDURX-UHFFFAOYSA-N n-(4-fluorophenyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine Chemical compound C1=CC(F)=CC=C1NC1=NC=NC2=C1CCC2 OZZPXKTXAWDURX-UHFFFAOYSA-N 0.000 description 1
- JFMYHTNZHKKFNE-UHFFFAOYSA-N n-(4-iodophenyl)-5,6-dimethylpyrimidin-4-amine Chemical compound CC1=NC=NC(NC=2C=CC(I)=CC=2)=C1C JFMYHTNZHKKFNE-UHFFFAOYSA-N 0.000 description 1
- ZQJLIIIORGJTFK-UHFFFAOYSA-N n-[4-chloro-3-(trifluoromethyl)phenyl]-5,6-dimethylpyrimidin-4-amine Chemical compound CC1=NC=NC(NC=2C=C(C(Cl)=CC=2)C(F)(F)F)=C1C ZQJLIIIORGJTFK-UHFFFAOYSA-N 0.000 description 1
- MFQAEPUNLPQHSH-UHFFFAOYSA-N n-phenyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C=12CCCC2=NC=NC=1NC1=CC=CC=C1 MFQAEPUNLPQHSH-UHFFFAOYSA-N 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000004526 pharmaceutical effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56086555A JPS57203072A (en) | 1981-06-05 | 1981-06-05 | 4-anilinopyrimidine derivative, its preparation, antidepressant comprising it as active ingredient |
| JP8655581 | 1981-06-05 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI821990A0 FI821990A0 (fi) | 1982-06-04 |
| FI77454B FI77454B (fi) | 1988-11-30 |
| FI77454C true FI77454C (fi) | 1989-03-10 |
Family
ID=13890246
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI821990A FI77454C (fi) | 1981-06-05 | 1982-06-04 | Foerfarande foer framstaellning av som laekemedel anvaendbara 4-anilino-pyrimidinderivat. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4450162A (en:Method) |
| EP (1) | EP0067630B1 (en:Method) |
| JP (1) | JPS57203072A (en:Method) |
| KR (1) | KR880002234B1 (en:Method) |
| CA (1) | CA1169861A (en:Method) |
| DE (1) | DE3263653D1 (en:Method) |
| ES (1) | ES8307760A1 (en:Method) |
| FI (1) | FI77454C (en:Method) |
| PH (1) | PH20130A (en:Method) |
| ZA (1) | ZA823917B (en:Method) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK130584A (da) * | 1983-04-08 | 1984-10-09 | Ciba Geigy Ag | N-(2-nitrophenyl)-4-amino-pyrimidin-derivater samt deres fremstilling og anvendelse som mikrobicider |
| PH21918A (en) * | 1983-07-25 | 1988-04-08 | Ciba Geigy Ag | N-(2-nitrophenyl)-5-aminopyrimidine derivatives,the preparation and use thereof |
| EP0139613A1 (de) * | 1983-08-29 | 1985-05-02 | Ciba-Geigy Ag | N-(2-Nitrophenyl)-4-aminopyrimidin-Derivate, deren Herstellung und Verwendung |
| US4725600A (en) * | 1984-07-13 | 1988-02-16 | Fujisawa Pharmaceutical Co., Ltd. | Pyrimidine compounds having activity as a cardiotonic anti-hypertensive cerebrovascular vasodilator and anti-platelet aggregation agent |
| JPS6270A (ja) * | 1985-03-07 | 1987-01-06 | Sankyo Co Ltd | シクロペンタ〔ｄ〕ピリミジン誘導体 |
| DE3618353A1 (de) * | 1986-05-31 | 1987-12-03 | Hoechst Ag | Schaedlingsbekaempfungsmittel auf der basis von aminopyrimidin-derivaten sowie neue aminopyrimidin-verbindungen |
| US5037980A (en) * | 1988-04-18 | 1991-08-06 | American Cyanamid Company | Phenyl imidazo[1,2-a]pyrimidines |
| GR900100380A (el) * | 1989-05-20 | 1991-10-10 | Fisons Plc | Μέ?οδος παρασκευής αντι-φλεγμονωδών παραγώγων αμινοφενόλης. |
| US5234936A (en) * | 1991-10-24 | 1993-08-10 | American Home Products Corporation | Pyrimidocycloalkanes as a ii antagonists |
| KR100262254B1 (ko) * | 1992-10-05 | 2000-07-15 | 나카히로 마오미 | 피리미딘 화합물 |
| WO1999050250A1 (en) * | 1998-03-27 | 1999-10-07 | Janssen Pharmaceutica N.V. | Hiv inhibiting pyrimidine derivatives |
| KR100643419B1 (ko) * | 1998-03-27 | 2006-11-10 | 얀센 파마슈티카 엔.브이. | Ｈｉｖ를 억제하는 피리미딘 유도체 |
| BRPI0014271B1 (pt) | 1999-09-24 | 2021-06-22 | Janssen Pharmaceutica N.V. | Partícula consistindo em uma dispersão de sólidos, uso da dita partícula, dispersão de sólidos, forma de dosagem farmacêutica, bem como processos de preparação de dita partícula, dispersão e forma de dosagem |
| ATE374190T1 (de) * | 2003-08-12 | 2007-10-15 | Hoffmann La Roche | Tetrahydrochinazolinderivate als cfr-antagonisten |
| WO2006055831A2 (en) | 2004-11-17 | 2006-05-26 | Miikana Therapeutics, Inc. | Kinase inhibitors |
| KR101487027B1 (ko) * | 2005-09-30 | 2015-01-28 | 미카나 테라퓨틱스, 인크. | 치환된 피라졸 화합물 |
| WO2008154026A1 (en) * | 2007-06-11 | 2008-12-18 | Miikana Therapeutics, Inc. | Substituted pyrazole compounds |
| US8946239B2 (en) | 2008-07-10 | 2015-02-03 | Duquesne University Of The Holy Spirit | Substituted pyrrolo, -furano, and cyclopentylpyrimidines having antimitotic and/or antitumor activity and methods of use thereof |
| EP3125897A4 (en) * | 2014-04-03 | 2017-11-15 | Duquesne University of the Holy Spirit | Substituted cyclopenta pyrimidine bicyclic compounds having antimitotic and/or antitumor activity and methods of use thereof |
| GB2553716B (en) | 2015-04-17 | 2020-06-17 | Univ Holy Ghost Duquesne | Pyrrolopyrimidines as antitumor agents |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2719846A (en) * | 1954-05-06 | 1955-10-04 | Searle & Co | 4[n-(beta-diethylaminoethyl) anilino]-pyrimidine and acid addition salts thereof |
| US3321478A (en) * | 1963-09-20 | 1967-05-23 | American Cyanamid Co | Aminoethoxyphenyl amine, ether, and sulfide derivatives of pyrimidine |
| FR2190818B1 (en:Method) * | 1972-06-28 | 1975-03-07 | Roussel Uclaf | |
| CH593266A5 (en:Method) * | 1973-09-20 | 1977-11-30 | Delalande Sa | |
| DE2626495A1 (de) * | 1976-06-12 | 1977-12-29 | Bayer Ag | Quartaere reaktivverbindungen |
-
1981
- 1981-06-05 JP JP56086555A patent/JPS57203072A/ja active Granted
-
1982
- 1982-05-31 PH PH27381A patent/PH20130A/en unknown
- 1982-06-02 US US06/384,416 patent/US4450162A/en not_active Expired - Fee Related
- 1982-06-03 DE DE8282302870T patent/DE3263653D1/de not_active Expired
- 1982-06-03 EP EP82302870A patent/EP0067630B1/en not_active Expired
- 1982-06-04 CA CA000404529A patent/CA1169861A/en not_active Expired
- 1982-06-04 ES ES512880A patent/ES8307760A1/es not_active Expired
- 1982-06-04 ZA ZA823917A patent/ZA823917B/xx unknown
- 1982-06-04 FI FI821990A patent/FI77454C/fi not_active IP Right Cessation
- 1982-06-04 KR KR8202513A patent/KR880002234B1/ko not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI821990A0 (fi) | 1982-06-04 |
| FI77454B (fi) | 1988-11-30 |
| US4450162A (en) | 1984-05-22 |
| ZA823917B (en) | 1983-04-27 |
| CA1169861A (en) | 1984-06-26 |
| JPS57203072A (en) | 1982-12-13 |
| KR840000508A (ko) | 1984-02-22 |
| EP0067630A1 (en) | 1982-12-22 |
| PH20130A (en) | 1986-10-02 |
| ES512880A0 (es) | 1983-08-01 |
| ES8307760A1 (es) | 1983-08-01 |
| KR880002234B1 (ko) | 1988-10-20 |
| JPH0440347B2 (en:Method) | 1992-07-02 |
| EP0067630B1 (en) | 1985-05-08 |
| DE3263653D1 (en) | 1985-06-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: SANKYO COMPANY LIMITED Owner name: UBE INDUSTRIES LTD. |