FI67699C - Foerfarande foer framstaellning av 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolinhydroklorid med blodtryckssaenkande verkan - Google Patents
Foerfarande foer framstaellning av 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolinhydroklorid med blodtryckssaenkande verkan Download PDFInfo
- Publication number
- FI67699C FI67699C FI790320A FI790320A FI67699C FI 67699 C FI67699 C FI 67699C FI 790320 A FI790320 A FI 790320A FI 790320 A FI790320 A FI 790320A FI 67699 C FI67699 C FI 67699C
- Authority
- FI
- Finland
- Prior art keywords
- furoyl
- piperazinyl
- dimethoxy
- amino
- yield
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 8
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 8
- 235000019270 ammonium chloride Nutrition 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- WFXFYZULCQKPIP-UHFFFAOYSA-N prazosin hydrochloride Chemical compound [H+].[Cl-].N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 WFXFYZULCQKPIP-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- -1 3,4-dimethoxy-6-cyano-phenyl Chemical group 0.000 claims description 2
- MXWBCRALMDQINL-UHFFFAOYSA-N n-(2-cyano-4,5-dimethoxyphenyl)-4-(furan-2-carbonyl)-n-methylpiperazine-1-carbothioamide Chemical compound C1=C(OC)C(OC)=CC(C#N)=C1N(C)C(=S)N1CCN(C(=O)C=2OC=CC=2)CC1 MXWBCRALMDQINL-UHFFFAOYSA-N 0.000 claims description 2
- 229960002386 prazosin hydrochloride Drugs 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 238000004128 high performance liquid chromatography Methods 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- 239000005708 Sodium hypochlorite Substances 0.000 claims 1
- 230000003276 anti-hypertensive effect Effects 0.000 claims 1
- 229910001873 dinitrogen Inorganic materials 0.000 claims 1
- 239000003480 eluent Substances 0.000 claims 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 229960001289 prazosin Drugs 0.000 description 7
- 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 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 4
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- BJAYMNUBIULRMF-UHFFFAOYSA-N 2-amino-4,5-dimethoxybenzonitrile Chemical compound COC1=CC(N)=C(C#N)C=C1OC BJAYMNUBIULRMF-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- SADPINFEWFPMEA-UHFFFAOYSA-N furan-2-yl(piperazin-1-yl)methanone Chemical compound C=1C=COC=1C(=O)N1CCNCC1 SADPINFEWFPMEA-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- 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
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/84—Nitrogen atoms
-
- 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
- Cephalosporin Compounds (AREA)
Priority Applications (22)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI790320A FI67699C (fi) | 1979-01-31 | 1979-01-31 | Foerfarande foer framstaellning av 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolinhydroklorid med blodtryckssaenkande verkan |
| NO794279A NO152298C (no) | 1979-01-31 | 1979-12-27 | Fremgangsmaate til fremstilling av 6,7-dimetoksy-4-amino-2-(4-(furoyl)-1-piperazinyl)-kinazolin-hydroklorid |
| US06/110,589 US4271300A (en) | 1979-01-31 | 1980-01-09 | Method for producing 6,7-dimethoxy-4-amino-2-[4-(2-furoyl)-1-piperazinyl] qu |
| CA343,361A CA1128945A (en) | 1979-01-31 | 1980-01-09 | Method for producing 6,7-dimethoxy-4-amino- 2-/4-(2-furoyl)-1-piperazinyl/ quinazoline hydrochloride having an antihypertensive effect |
| CH12180A CH644605A5 (de) | 1979-01-31 | 1980-01-09 | Verfahren zur herstellung von blutdrucksenkendem 6,7-dimethoxy-4-amino-2-(4-(2-furoyl)-1-piperazinyl)chinazolinhydrochlorid. |
| YU58/80A YU41498B (en) | 1979-01-31 | 1980-01-10 | Proces for obtaining 6,7-dimethoxy-4-amino-2-(4-(2-furoyl)-1-piperazinyl)-guinazoline chlorohydrate of an antihypertensive effec |
| SI8010058A SI8010058A8 (sl) | 1979-01-31 | 1980-01-10 | Postopek za prodobivanje 6,7-dimetoksi-4-amino-2-/4-(2-furoil)-piperazinil/-kinazolin klorhidrata z antihipertenzivnim učinkom |
| AT0019580A AT374475B (de) | 1979-01-31 | 1980-01-15 | Verfahren zur herstellung von blutdrucksenkendem 6,7-dimethoxy-4-amino-2-(4-(2-furoyl)-1piperazinyl) chinazolinhydrochlorid |
| NL8000289A NL190701C (nl) | 1979-01-31 | 1980-01-16 | Werkwijze voor de bereiding van 6,7-dimethoxy-4-amino-2-[4-(2-furoyl)-1-piperazinyl]chinazolinehydrochloride. |
| BE0/199070A BE881297A (fr) | 1979-01-31 | 1980-01-23 | Procede pour la fabrication de chlorhydrate de 6,7-dimethoxy-4-amino-2- 4-(2-furoyl)-1-piperazinyl quinazoline ayant un effet antihypertensif |
| DE19803002553 DE3002553A1 (de) | 1979-01-31 | 1980-01-25 | Verfahren zur herstellung von 6,7- dimethoxy-4-amino-2-eckige klammer auf 4-(2-furoyl)-1-piperazinyl eckige klammer zu chinazolinhydrochlorid |
| CS80588A CS214692B2 (en) | 1979-01-31 | 1980-01-28 | Method of making the hydrochloride of 6,7-dimethoxy-4-amino-2-+l4-+l2-furoyl+p-1-piperazinyl+pchnazoline |
| ZA00800501A ZA80501B (en) | 1979-01-31 | 1980-01-28 | Method for producing 6,7-dimethoxy-4-amino-2-(4-(2-furoyl)-1-piperazinyl)quinazoline hydrochloride having an antihypertensive effect |
| GB8002903A GB2041932B (en) | 1979-01-31 | 1980-01-29 | Method for producing 6,7-dimethoxy-4-amino-2-(4-(2-furoyl)-1-piper-azinyl) quinazoline hydrochloride |
| HU8080182A HU181016B (en) | 1979-01-31 | 1980-01-29 | Process for producing 6,7-dimethoxy-5-amino-2-square bracket-4-bracket-2-furoyl-bracket closed-1-piperazinyl-square bracket c.osed-quinazoline hydrochlokike |
| PL1980221684A PL126994B1 (en) | 1979-01-31 | 1980-01-30 | Method for producing 6,7-dimethoxy-4-amino-2-/4-(2-furoyl)-1-piperazinyl/-quinazoline hydrochloride |
| SU802874898A SU900812A3 (ru) | 1979-01-31 | 1980-01-30 | Способ получени гидрохлорида 6,7-диметокси-4-амино-2-[4-(2-фуроил)-1-пиперазинил-ХИНАЗОЛИНА |
| FR8001991A FR2447920A1 (fr) | 1979-01-31 | 1980-01-30 | Procede pour la fabrication de chlorhydrate de 6,7-dimethoxy-4-amino-2-(4-(2-furoyl)-1-piperazinyl)quinazoline ayant un effet antihypertensif |
| JP1081580A JPS55104280A (en) | 1979-01-31 | 1980-01-30 | Manufacture of 6*77dimethoxyy44aminoo22 *44*22furoyl**11piperazinyl*quinazoline hydrochloride |
| DD80218776A DD148952A1 (de) | 1979-01-31 | 1980-01-31 | Verfahren zur herstellung von blutdrucksenkendem 6,7-dimethoxy-4-amino-2- eckige klammer auf 4-(2-furoyl)-1-piperazinyl eckige klammer zu chinazolinhydrochlorid |
| DK042680A DK158352C (da) | 1979-01-31 | 1980-01-31 | Fremgangsmaade til fremstilling af 6,7-dimethoxy-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolinhydrochlorid |
| SE8000777A SE430692B (sv) | 1979-01-31 | 1980-01-31 | Sett att framstella 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-1-piperazinyl) kinazolinhydroklorid med antihypertensiv verkan |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI790320 | 1979-01-31 | ||
| FI790320A FI67699C (fi) | 1979-01-31 | 1979-01-31 | Foerfarande foer framstaellning av 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolinhydroklorid med blodtryckssaenkande verkan |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI790320A FI790320A (fi) | 1980-08-01 |
| FI67699B FI67699B (fi) | 1985-01-31 |
| FI67699C true FI67699C (fi) | 1985-05-10 |
Family
ID=8512343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI790320A FI67699C (fi) | 1979-01-31 | 1979-01-31 | Foerfarande foer framstaellning av 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolinhydroklorid med blodtryckssaenkande verkan |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4271300A (no) |
| JP (1) | JPS55104280A (no) |
| AT (1) | AT374475B (no) |
| BE (1) | BE881297A (no) |
| CA (1) | CA1128945A (no) |
| CH (1) | CH644605A5 (no) |
| CS (1) | CS214692B2 (no) |
| DD (1) | DD148952A1 (no) |
| DE (1) | DE3002553A1 (no) |
| DK (1) | DK158352C (no) |
| FI (1) | FI67699C (no) |
| FR (1) | FR2447920A1 (no) |
| GB (1) | GB2041932B (no) |
| HU (1) | HU181016B (no) |
| NL (1) | NL190701C (no) |
| NO (1) | NO152298C (no) |
| PL (1) | PL126994B1 (no) |
| SE (1) | SE430692B (no) |
| SU (1) | SU900812A3 (no) |
| YU (1) | YU41498B (no) |
| ZA (1) | ZA80501B (no) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI70411C (fi) * | 1980-12-29 | 1986-09-19 | Pfizer | Foerfarande foer framstaellning av nya antihypertensiva 4-amino-6,7-dimetoxi-2-piperazinokinazolin derivat |
| FI79107C (fi) * | 1984-06-25 | 1989-11-10 | Orion Yhtymae Oy | Foerfarande foer framstaellning av stabil -form av prazosinhydroklorid. |
| US4601897A (en) * | 1985-11-06 | 1986-07-22 | Pfizer Inc. | Prazosin-pirbuterol combination for bronchodilation |
| AT384218B (de) * | 1985-12-04 | 1987-10-12 | Gerot Pharmazeutika | Verfahren zur herstellung von neuen chinazolin-derivaten |
| YU70890A (en) * | 1989-04-21 | 1992-05-28 | Egyt Gyogyszervegyeszeti Gyar | Process for obtaining quinazoline derivatives |
| CA2077252C (en) * | 1992-08-31 | 2001-04-10 | Khashayar Karimian | Methods of making ureas and guanidines, and intermediates therefor |
Family Cites Families (6)
| 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 |
| GB1390015A (en) * | 1971-05-07 | 1975-04-09 | Koninklijke Pharma Fab Nv | 4-amino-quinazoline compounds |
| US3935213A (en) * | 1973-12-05 | 1976-01-27 | Pfizer Inc. | Process for hypotensive 4-amino-2-(piperazin-1-yl) quinazoline derivatives |
| US4092315A (en) * | 1976-03-01 | 1978-05-30 | Pfizer Inc. | Novel crystalline forms of prazosin hydrochloride |
| FI58124C (fi) * | 1976-12-15 | 1980-12-10 | Orion Yhtymae Oy | Ny mellanprodukt 3,4-dimetoxi-6-(4-(2-furoyl)-1-piperazinyltiokarbamido)-bensonitril foer framstaellning av 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolin med blodtryckssaenkande verkan |
| FI58125C (fi) * | 1976-12-15 | 1985-01-02 | Orion Yhtymae Oy | Foerfarande foer framstaellning av 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolin med blodtryckssaenkande vekan |
-
1979
- 1979-01-31 FI FI790320A patent/FI67699C/fi not_active IP Right Cessation
- 1979-12-27 NO NO794279A patent/NO152298C/no unknown
-
1980
- 1980-01-09 CA CA343,361A patent/CA1128945A/en not_active Expired
- 1980-01-09 US US06/110,589 patent/US4271300A/en not_active Expired - Lifetime
- 1980-01-09 CH CH12180A patent/CH644605A5/de not_active IP Right Cessation
- 1980-01-10 YU YU58/80A patent/YU41498B/xx unknown
- 1980-01-15 AT AT0019580A patent/AT374475B/de not_active IP Right Cessation
- 1980-01-16 NL NL8000289A patent/NL190701C/xx not_active IP Right Cessation
- 1980-01-23 BE BE0/199070A patent/BE881297A/fr not_active IP Right Cessation
- 1980-01-25 DE DE19803002553 patent/DE3002553A1/de active Granted
- 1980-01-28 ZA ZA00800501A patent/ZA80501B/xx unknown
- 1980-01-28 CS CS80588A patent/CS214692B2/cs unknown
- 1980-01-29 GB GB8002903A patent/GB2041932B/en not_active Expired
- 1980-01-29 HU HU8080182A patent/HU181016B/hu not_active IP Right Cessation
- 1980-01-30 PL PL1980221684A patent/PL126994B1/pl unknown
- 1980-01-30 FR FR8001991A patent/FR2447920A1/fr active Granted
- 1980-01-30 SU SU802874898A patent/SU900812A3/ru active
- 1980-01-30 JP JP1081580A patent/JPS55104280A/ja active Granted
- 1980-01-31 DK DK042680A patent/DK158352C/da not_active IP Right Cessation
- 1980-01-31 DD DD80218776A patent/DD148952A1/de not_active IP Right Cessation
- 1980-01-31 SE SE8000777A patent/SE430692B/sv unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS214692B2 (en) | 1982-05-28 |
| NO152298B (no) | 1985-05-28 |
| CH644605A5 (de) | 1984-08-15 |
| PL221684A1 (no) | 1980-10-20 |
| ATA19580A (de) | 1983-09-15 |
| DK158352C (da) | 1990-10-08 |
| SE430692B (sv) | 1983-12-05 |
| SE8000777L (sv) | 1980-08-01 |
| NL190701C (nl) | 1994-07-01 |
| DE3002553C2 (no) | 1988-10-27 |
| BE881297A (fr) | 1980-05-16 |
| AT374475B (de) | 1984-04-25 |
| NO152298C (no) | 1985-09-04 |
| PL126994B1 (en) | 1983-09-30 |
| FR2447920A1 (fr) | 1980-08-29 |
| FI67699B (fi) | 1985-01-31 |
| NL190701B (nl) | 1994-02-01 |
| ZA80501B (en) | 1981-02-25 |
| FR2447920B1 (no) | 1982-12-03 |
| JPS55104280A (en) | 1980-08-09 |
| DK158352B (da) | 1990-05-07 |
| YU41498B (en) | 1987-08-31 |
| GB2041932A (en) | 1980-09-17 |
| GB2041932B (en) | 1982-10-27 |
| US4271300A (en) | 1981-06-02 |
| NO794279L (no) | 1980-08-01 |
| DE3002553A1 (de) | 1980-08-07 |
| DD148952A1 (de) | 1981-06-17 |
| JPS6310955B2 (no) | 1988-03-10 |
| YU5880A (en) | 1983-02-28 |
| DK42680A (da) | 1980-08-01 |
| HU181016B (en) | 1983-05-30 |
| SU900812A3 (ru) | 1982-01-23 |
| FI790320A (fi) | 1980-08-01 |
| CA1128945A (en) | 1982-08-03 |
| NL8000289A (nl) | 1980-08-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: ORION-YHTYMAE OY |