FI66610C - Foerfarande foer framstaellning av 2-(4-furoylpiperazin-1-yl)-4-amino-6,7-dimetoxikinazolin - Google Patents
Foerfarande foer framstaellning av 2-(4-furoylpiperazin-1-yl)-4-amino-6,7-dimetoxikinazolin Download PDFInfo
- Publication number
- FI66610C FI66610C FI772629A FI772629A FI66610C FI 66610 C FI66610 C FI 66610C FI 772629 A FI772629 A FI 772629A FI 772629 A FI772629 A FI 772629A FI 66610 C FI66610 C FI 66610C
- Authority
- FI
- Finland
- Prior art keywords
- amino
- formula
- dimethoxyquinazoline
- reaction
- furyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 19
- -1 4-FUROYLPIPERAZIN-1-YL Chemical class 0.000 title description 17
- 150000001875 compounds Chemical class 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 4
- IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- DJDBLBBSUAQYAA-UHFFFAOYSA-N piperazine-1-carbonitrile Chemical compound N#CN1CCNCC1 DJDBLBBSUAQYAA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- IFLGOTCDGFFWFY-UHFFFAOYSA-N [Na]C1=CC=CO1 Chemical compound [Na]C1=CC=CO1 IFLGOTCDGFFWFY-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ROBVTMWEQLGULZ-UHFFFAOYSA-N 4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazine-1-carbonitrile Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N1CCN(C#N)CC1 ROBVTMWEQLGULZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- KCTBOHUTRYYLJA-UHFFFAOYSA-N lithium;2h-furan-2-ide Chemical compound [Li+].C=1C=[C-]OC=1 KCTBOHUTRYYLJA-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- LXWLEQZDXOQZGW-UHFFFAOYSA-N 3-bromofuran Chemical compound BrC=1C=COC=1 LXWLEQZDXOQZGW-UHFFFAOYSA-N 0.000 description 2
- APKHJGDGWQDBGM-UHFFFAOYSA-N 6,7-dimethoxy-2-piperazin-1-ylquinazolin-4-amine Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N1CCNCC1 APKHJGDGWQDBGM-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 229960001289 prazosin Drugs 0.000 description 2
- OWMHBKYAOYHOQK-UHFFFAOYSA-N sodium;methanidylbenzene Chemical compound [Na+].[CH2-]C1=CC=CC=C1 OWMHBKYAOYHOQK-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 1
- ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical compound COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 description 1
- OYMCMWPHMPODNK-UHFFFAOYSA-N 2-bromofuran Chemical compound BrC1=CC=CO1 OYMCMWPHMPODNK-UHFFFAOYSA-N 0.000 description 1
- ZMGPXECXBVFPBO-UHFFFAOYSA-N 2-chloro-6,7,8-trimethoxyquinazolin-4-amine Chemical compound N1=C(Cl)N=C2C(OC)=C(OC)C(OC)=CC2=C1N ZMGPXECXBVFPBO-UHFFFAOYSA-N 0.000 description 1
- HWIIAAVGRHKSOJ-UHFFFAOYSA-N 2-chloro-6,7-dimethoxyquinazolin-4-amine Chemical compound ClC1=NC(N)=C2C=C(OC)C(OC)=CC2=N1 HWIIAAVGRHKSOJ-UHFFFAOYSA-N 0.000 description 1
- RHISQWTXRCBOBJ-UHFFFAOYSA-N 6,7,8-trimethoxyquinazoline Chemical class N1=CN=C2C(OC)=C(OC)C(OC)=CC2=C1 RHISQWTXRCBOBJ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- BQZGSABSYDYXHI-UHFFFAOYSA-N [Na]C=1C=COC=1 Chemical compound [Na]C=1C=COC=1 BQZGSABSYDYXHI-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229940045348 brown mixture Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000019837 monoammonium phosphate Nutrition 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 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
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/724,707 US4062844A (en) | 1976-09-20 | 1976-09-20 | Process for preparing hypotensive 2-(4-aroylpiperazin-1-yl)-amino-6,7-dimethoxyquinazolines |
| US72470776 | 1976-09-20 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI772629A7 FI772629A7 (fi) | 1978-03-21 |
| FI66610B FI66610B (fi) | 1984-07-31 |
| FI66610C true FI66610C (fi) | 1984-11-12 |
Family
ID=24911552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI772629A FI66610C (fi) | 1976-09-20 | 1977-09-05 | Foerfarande foer framstaellning av 2-(4-furoylpiperazin-1-yl)-4-amino-6,7-dimetoxikinazolin |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US4062844A (xx) |
| JP (1) | JPS5337676A (xx) |
| AR (1) | AR213659A1 (xx) |
| AT (1) | AT357542B (xx) |
| AU (1) | AU500908B2 (xx) |
| BE (1) | BE858844A (xx) |
| BG (1) | BG28054A3 (xx) |
| CA (1) | CA1068699A (xx) |
| CH (1) | CH632507A5 (xx) |
| CS (1) | CS203172B2 (xx) |
| DD (1) | DD132661A5 (xx) |
| DE (1) | DE2740331C3 (xx) |
| DK (1) | DK143340C (xx) |
| ES (1) | ES462146A1 (xx) |
| FI (1) | FI66610C (xx) |
| FR (1) | FR2364918A1 (xx) |
| GB (1) | GB1543668A (xx) |
| GR (1) | GR69792B (xx) |
| HK (1) | HK31181A (xx) |
| HU (1) | HU180041B (xx) |
| IE (1) | IE45966B1 (xx) |
| LU (1) | LU78149A1 (xx) |
| MY (1) | MY8100266A (xx) |
| NL (1) | NL189132C (xx) |
| NO (1) | NO147423C (xx) |
| PL (1) | PL105830B1 (xx) |
| PT (1) | PT67006B (xx) |
| RO (1) | RO73051A (xx) |
| SE (1) | SE435381B (xx) |
| SU (1) | SU847919A3 (xx) |
| YU (1) | YU39155B (xx) |
| ZA (1) | ZA775098B (xx) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0022481A1 (en) * | 1979-06-21 | 1981-01-21 | Mitsubishi Yuka Pharmaceutical Co., Ltd. | 5,6-Alkylenepyrimidine derivatives, processes for preparing the same and pharmaceutical compositions |
| US4607034A (en) * | 1979-10-29 | 1986-08-19 | Mitsubishi Yuka Pharmaceutical Co., Ltd. | Quinazoline derivatives and pharmaceutical composition thereof |
| JPS5793977A (en) * | 1980-11-26 | 1982-06-11 | Sankyo Co Ltd | Acylaminoquinazoline derivative and its preparation |
| FI70411C (fi) * | 1980-12-29 | 1986-09-19 | Pfizer | Foerfarande foer framstaellning av nya antihypertensiva 4-amino-6,7-dimetoxi-2-piperazinokinazolin derivat |
| US4625012A (en) * | 1985-08-26 | 1986-11-25 | Essex Specialty Products, Inc. | Moisture curable polyurethane polymers |
| IT1270993B (it) * | 1994-03-18 | 1997-05-26 | Recordati Chem Pharm | Derivati chinzolilamminici attivi come alfa-antagonisti |
| GB9708917D0 (en) * | 1997-05-01 | 1997-06-25 | Pfizer Ltd | Compounds useful in therapy |
| US6313294B1 (en) | 1998-02-04 | 2001-11-06 | Development Center For Biotechnology | Process for preparing amides |
| WO2025006391A1 (en) * | 2023-06-26 | 2025-01-02 | Athos Therapeutics, Inc. | Small molecules for the treatment of autoimmune disorders |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3511836A (en) * | 1967-12-13 | 1970-05-12 | Pfizer & Co C | 2,4,6,7-tetra substituted quinazolines |
| US3935213A (en) * | 1973-12-05 | 1976-01-27 | Pfizer Inc. | Process for hypotensive 4-amino-2-(piperazin-1-yl) quinazoline derivatives |
-
1976
- 1976-09-20 US US05/724,707 patent/US4062844A/en not_active Expired - Lifetime
-
1977
- 1977-08-05 SE SE7708942A patent/SE435381B/xx not_active IP Right Cessation
- 1977-08-22 CA CA285,258A patent/CA1068699A/en not_active Expired
- 1977-08-23 GR GR54218A patent/GR69792B/el unknown
- 1977-08-23 ZA ZA00775098A patent/ZA775098B/xx unknown
- 1977-08-25 AU AU28221/77A patent/AU500908B2/en not_active Expired
- 1977-09-02 YU YU02096/77A patent/YU39155B/xx unknown
- 1977-09-05 DE DE2740331A patent/DE2740331C3/de not_active Expired
- 1977-09-05 FI FI772629A patent/FI66610C/fi not_active IP Right Cessation
- 1977-09-05 NL NLAANVRAGE7709736,A patent/NL189132C/xx not_active IP Right Cessation
- 1977-09-05 AT AT636877A patent/AT357542B/de not_active IP Right Cessation
- 1977-09-06 PT PT67006A patent/PT67006B/pt unknown
- 1977-09-06 DK DK395877A patent/DK143340C/da not_active IP Right Cessation
- 1977-09-06 ES ES462146A patent/ES462146A1/es not_active Expired
- 1977-09-06 NO NO773073A patent/NO147423C/no unknown
- 1977-09-06 CH CH1089477A patent/CH632507A5/de not_active IP Right Cessation
- 1977-09-07 AR AR269118A patent/AR213659A1/es active
- 1977-09-07 PL PL1977200710A patent/PL105830B1/pl unknown
- 1977-09-13 CS CS775951A patent/CS203172B2/cs unknown
- 1977-09-19 RO RO7791610A patent/RO73051A/ro unknown
- 1977-09-19 HU HU77PI591A patent/HU180041B/hu not_active IP Right Cessation
- 1977-09-19 FR FR7728152A patent/FR2364918A1/fr active Granted
- 1977-09-19 GB GB38962/77A patent/GB1543668A/en not_active Expired
- 1977-09-19 BE BE181026A patent/BE858844A/xx not_active IP Right Cessation
- 1977-09-19 SU SU772522448A patent/SU847919A3/ru active
- 1977-09-19 IE IE1910/77A patent/IE45966B1/en not_active IP Right Cessation
- 1977-09-20 LU LU78149A patent/LU78149A1/xx unknown
- 1977-09-20 DD DD7700201112A patent/DD132661A5/xx unknown
- 1977-09-20 BG BG037373A patent/BG28054A3/xx unknown
- 1977-09-20 JP JP11317677A patent/JPS5337676A/ja active Pending
-
1981
- 1981-07-02 HK HK311/81A patent/HK31181A/xx unknown
- 1981-12-30 MY MY266/81A patent/MY8100266A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI77455C (fi) | Foerfarande foer framstaellning av antihypertensiva 2,4-diaminokinazolinfoereningar. | |
| JP2556722B2 (ja) | 新規なスルホンアミド化合物 | |
| FI66610C (fi) | Foerfarande foer framstaellning av 2-(4-furoylpiperazin-1-yl)-4-amino-6,7-dimetoxikinazolin | |
| FI59799B (fi) | Nytt foerfarande foer framstaellning av 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-piperazin-1-yl)-kinazolin foer anvaendning som ett antihypertensivt medel | |
| CN115894443B (zh) | 一种化合物艾奎斯韦及其应用 | |
| WO1994005628A1 (en) | Synthesis of 2-substituted quinazoline compounds (such as terazosin) and meobentine and bethanidine and intermediates therefor | |
| US4115569A (en) | Cyclic diamine derivatives | |
| CA1069505A (en) | Process for preparing 1-polyhaloalkyl-3, 4-dihydro-2-(1h)-quinazolinones | |
| US4575553A (en) | Antitumor m-AMSA analog | |
| CZ299163B6 (cs) | Zpusob prípravy 1,3-disubstituovaných-4-oxocyklických mocovin | |
| FI66853B (fi) | Mellanprodukt foer anvaendning vid framstaellning av hypotensivt 2-(4-(2-furoyl)piperazin-1-yl)-6,7-dimetoxikinazolin | |
| Fodor et al. | Synthesis and structural characterisation of 4H‐1, 3‐benzothiazine derivatives | |
| EP0146642B1 (de) | Verfahren zur Herstellung von 4-Amino-6,7-dimethoxy-2-(4-(furo-2-yl)-piperazin-1-yl)-chinazolin und dessen physiologisch annehmbarer Salze | |
| US4927970A (en) | Substituted 3-cyclobutene-1,2-dione intermediates | |
| Kobayashi et al. | Synthesis of 4-(1-Dialkylaminoalkyl)-pyrrolo (1, 2-a) quinoxalines | |
| US4091095A (en) | Phosphinyl compounds | |
| Katritzky et al. | A General and Convenient Synthesis of N-[(1. Diphenyl-oxophosphinyl) alkyl] carboxamides and Sulfamide | |
| KR890004558B1 (ko) | 4-아미노-6,7-디 메톡시 퀴나졸린 유도체의 제조방법 | |
| JPS62155268A (ja) | ナイザチジンの合成法 | |
| EP0080721A2 (en) | Diphenylalkanoamine derivatives, and their production and use | |
| EP0314483A1 (en) | Preparation of benzamides | |
| FI57590B (fi) | Saosom mellanprodukt vid framstaellning av blodtrycksnedsaettande 2-substituerade-4-amino-6,7,8-trialkoxikinazoliner anvaendbara-2-halogen-4-amino-6,7,8-trialkoxikinazoliner | |
| FI63943B (fi) | Vid framstaellning av 7-acylamido-3-(1-karboxi-laegre-alkyl-tetrazol-5-yltiometyl)-3-cefem-4-karboxylsyror och deras salter saosom mellanprodukter anvaendbara foereningar | |
| JPS5916879A (ja) | Ｎ−置換イミダゾ−ル類の製造法 | |
| KR820002385B1 (ko) | 이소퀴놀린 유도체의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: PFIZER INC. |