NO127580B - - Google Patents
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- Publication number
- NO127580B NO127580B NO02638/70A NO263870A NO127580B NO 127580 B NO127580 B NO 127580B NO 02638/70 A NO02638/70 A NO 02638/70A NO 263870 A NO263870 A NO 263870A NO 127580 B NO127580 B NO 127580B
- Authority
- NO
- Norway
- Prior art keywords
- lower alkyl
- atom
- trimethoxy
- optionally
- general formula
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- SDQJTWBNWQABLE-UHFFFAOYSA-N 1h-quinazoline-2,4-dione Chemical class C1=CC=C2C(=O)NC(=O)NC2=C1 SDQJTWBNWQABLE-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 229940072033 potash Drugs 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 9
- 235000015320 potassium carbonate Nutrition 0.000 description 9
- 238000000746 purification Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 4
- JMGOXQQBZOMKFG-UHFFFAOYSA-N methyl 2-isocyanato-3,4,5-trimethoxybenzoate Chemical compound COC1=C(C(=CC(=C1OC)OC)C(=O)OC)N=C=O JMGOXQQBZOMKFG-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000052 vinegar Substances 0.000 description 4
- 235000021419 vinegar Nutrition 0.000 description 4
- BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 3
- QNACMQOICPJEOM-UHFFFAOYSA-N 6,7,8-trimethoxy-1h-quinazoline-2,4-dione Chemical compound COC1=C(OC)C(OC)=CC2=C1NC(=O)NC2=O QNACMQOICPJEOM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- UPVUQELOASQBMY-UHFFFAOYSA-N methyl 2-amino-3,4,5-trimethoxybenzoate Chemical compound COC(=O)C1=CC(OC)=C(OC)C(OC)=C1N UPVUQELOASQBMY-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- JFCITVLHUMNYAL-UHFFFAOYSA-N 3,4,5-trimethoxy-2-nitrobenzoyl chloride Chemical compound [N+](=O)([O-])C1=C(C(=O)Cl)C=C(C(=C1OC)OC)OC JFCITVLHUMNYAL-UHFFFAOYSA-N 0.000 description 1
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical group CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000000916 dilatatory effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000007787 solid Substances 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
- C07D239/70—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
- C07D239/96—Two oxygen atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691934036 DE1934036A1 (de) | 1969-07-04 | 1969-07-04 | Basisch substituierte Derivate des 2,4-(1H,3H)-Chinazolindions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO127580B true NO127580B (de) | 1973-07-16 |
Family
ID=5738912
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO02638/70A NO127580B (de) | 1969-07-04 | 1970-07-03 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US3740398A (de) |
| AT (2) | AT297711B (de) |
| BE (1) | BE753009A (de) |
| BG (2) | BG17777A3 (de) |
| BR (1) | BR6915287D0 (de) |
| CA (1) | CA949971A (de) |
| CH (2) | CH551980A (de) |
| CS (1) | CS167924B2 (de) |
| DE (1) | DE1934036A1 (de) |
| DK (1) | DK124683B (de) |
| ES (2) | ES381402A1 (de) |
| FR (1) | FR2059481B1 (de) |
| GB (1) | GB1311543A (de) |
| IE (1) | IE34309B1 (de) |
| IL (1) | IL34741A (de) |
| NL (1) | NL7009211A (de) |
| NO (1) | NO127580B (de) |
| PL (1) | PL72734B1 (de) |
| RO (2) | RO62415A (de) |
| ZA (1) | ZA704558B (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1204071B (de) * | 1957-06-15 | 1965-10-28 | Dr Hans Thoma | Lagerung der Triebwelle einer Druckfluessigkeits-Axialkolbenmaschine |
| DE2050640A1 (de) * | 1970-10-15 | 1972-04-20 | Cassella Farbwerke Mainkur Ag, 6000 Frankfurt | Basisch substituierte Derivate des (lH,3H)-Chinazolin-2-thion-4-ons |
| US4263220A (en) * | 1979-02-02 | 1981-04-21 | The Dow Chemical Company | Alkylene dicyanates |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3274194A (en) * | 1963-03-29 | 1966-09-20 | Miles Lab | Quinazolinedione derivatives |
-
1969
- 1969-07-04 DE DE19691934036 patent/DE1934036A1/de active Pending
- 1969-12-17 BR BR215287/69A patent/BR6915287D0/pt unknown
-
1970
- 1970-06-16 IE IE782/70A patent/IE34309B1/xx unknown
- 1970-06-17 IL IL34741A patent/IL34741A/en unknown
- 1970-06-23 BG BG14998A patent/BG17777A3/xx unknown
- 1970-06-23 BG BG16572A patent/BG17572A3/xx unknown
- 1970-06-23 NL NL7009211A patent/NL7009211A/xx unknown
- 1970-06-25 US US00049923A patent/US3740398A/en not_active Expired - Lifetime
- 1970-06-25 DK DK331670AA patent/DK124683B/da unknown
- 1970-07-02 RO RO7000069978A patent/RO62415A/ro unknown
- 1970-07-02 RO RO63817A patent/RO57547A/ro unknown
- 1970-07-03 NO NO02638/70A patent/NO127580B/no unknown
- 1970-07-03 CH CH1013870A patent/CH551980A/de not_active IP Right Cessation
- 1970-07-03 BE BE753009D patent/BE753009A/xx unknown
- 1970-07-03 GB GB3238470A patent/GB1311543A/en not_active Expired
- 1970-07-03 ES ES381402A patent/ES381402A1/es not_active Expired
- 1970-07-03 FR FR7024774A patent/FR2059481B1/fr not_active Expired
- 1970-07-03 PL PL1970141807A patent/PL72734B1/pl unknown
- 1970-07-03 CA CA087,172A patent/CA949971A/en not_active Expired
- 1970-07-03 AT AT603570A patent/AT297711B/de not_active IP Right Cessation
- 1970-07-03 ES ES381403A patent/ES381403A1/es not_active Expired
- 1970-07-03 CH CH1013970A patent/CH551981A/de not_active IP Right Cessation
- 1970-07-03 AT AT603670A patent/AT296999B/de not_active IP Right Cessation
- 1970-07-03 ZA ZA704558A patent/ZA704558B/xx unknown
- 1970-07-06 CS CS4715A patent/CS167924B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES381403A1 (es) | 1973-03-16 |
| FR2059481A1 (de) | 1971-06-04 |
| NL7009211A (de) | 1971-01-06 |
| PL72734B1 (de) | 1974-08-30 |
| BG17572A3 (de) | 1973-11-10 |
| FR2059481B1 (de) | 1974-03-22 |
| IE34309B1 (en) | 1975-04-02 |
| GB1311543A (en) | 1973-03-28 |
| ZA704558B (en) | 1971-03-31 |
| RO62415A (fr) | 1977-10-15 |
| BG17777A3 (de) | 1973-12-25 |
| CS167924B2 (de) | 1976-05-28 |
| IL34741A (en) | 1973-03-30 |
| RO57547A (de) | 1975-02-15 |
| DE1934036A1 (de) | 1971-01-07 |
| CA949971A (en) | 1974-06-25 |
| BE753009A (fr) | 1971-01-04 |
| IE34309L (en) | 1971-01-04 |
| DK124683B (da) | 1972-11-13 |
| BR6915287D0 (pt) | 1973-04-19 |
| CH551981A (de) | 1974-07-31 |
| AT297711B (de) | 1972-04-10 |
| US3740398A (en) | 1973-06-19 |
| ES381402A1 (es) | 1973-04-01 |
| AT296999B (de) | 1972-03-10 |
| CH551980A (de) | 1974-07-31 |
| IL34741A0 (en) | 1970-08-19 |
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