CH563995A5 - 3, 4- dihydro-2 (1h)-quin azolinones - anti-inflammatories and analge - Google Patents
3, 4- dihydro-2 (1h)-quin azolinones - anti-inflammatories and analgeInfo
- Publication number
- CH563995A5 CH563995A5 CH35875A CH35875A CH563995A5 CH 563995 A5 CH563995 A5 CH 563995A5 CH 35875 A CH35875 A CH 35875A CH 35875 A CH35875 A CH 35875A CH 563995 A5 CH563995 A5 CH 563995A5
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- general formula
- radical
- alkoxy
- lower alkyl
- Prior art date
Links
- 230000003110 anti-inflammatory effect Effects 0.000 title description 3
- CTOUNZIAEBIWAW-UHFFFAOYSA-N 3,4-dihydro-1h-quinazolin-2-one Chemical class C1=CC=C2NC(=O)NCC2=C1 CTOUNZIAEBIWAW-UHFFFAOYSA-N 0.000 title 1
- 241001535291 Analges Species 0.000 title 1
- 229940121363 anti-inflammatory agent Drugs 0.000 title 1
- 239000002260 anti-inflammatory agent Substances 0.000 title 1
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 3
- 125000002541 furyl group Chemical group 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- -1 alkylsulfonyl radicals Chemical class 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 abstract description 2
- 125000004953 trihalomethyl group Chemical group 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- AZQAQRHOKWCEED-UHFFFAOYSA-N 1-(cyclopropylmethyl)-6-methyl-4-phenyl-3,4-dihydroquinazolin-2-one Chemical compound O=C1NC(C=2C=CC=CC=2)C2=CC(C)=CC=C2N1CC1CC1 AZQAQRHOKWCEED-UHFFFAOYSA-N 0.000 description 1
- RUVYXZNLBIJUHG-UHFFFAOYSA-N 1-(cyclopropylmethyl)-6-methylsulfanyl-4-phenyl-3,4-dihydroquinazolin-2-one Chemical compound O=C1NC(C=2C=CC=CC=2)C2=CC(SC)=CC=C2N1CC1CC1 RUVYXZNLBIJUHG-UHFFFAOYSA-N 0.000 description 1
- AKRYIVMCLZOZMJ-UHFFFAOYSA-N 1-(cyclopropylmethyl)-6-nitro-4-phenyl-3,4-dihydroquinazolin-2-one Chemical compound C1(CC1)CN1C(NC(C2=CC(=CC=C12)[N+](=O)[O-])C1=CC=CC=C1)=O AKRYIVMCLZOZMJ-UHFFFAOYSA-N 0.000 description 1
- FBZCJTWPDPBQNA-UHFFFAOYSA-N 6-chloro-1-(2-ethoxyethyl)-4-phenyl-3,4-dihydroquinazolin-2-one Chemical compound C(C)OCCN1C(NC(C2=CC(=CC=C12)Cl)C1=CC=CC=C1)=O FBZCJTWPDPBQNA-UHFFFAOYSA-N 0.000 description 1
- IZQMFHKDSGFZOO-UHFFFAOYSA-N 6-chloro-3,4-dihydro-1h-quinazolin-2-one Chemical compound N1C(=O)NCC2=CC(Cl)=CC=C21 IZQMFHKDSGFZOO-UHFFFAOYSA-N 0.000 description 1
- KBZITYIDKPBARR-UHFFFAOYSA-N 6-methoxy-4-phenyl-1-(2,2,2-trifluoroethyl)-3,4-dihydroquinazolin-2-one Chemical compound C12=CC(OC)=CC=C2N(CC(F)(F)F)C(=O)NC1C1=CC=CC=C1 KBZITYIDKPBARR-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 compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- NYQWTGSPKJLMIH-UHFFFAOYSA-N C(C)OCCN1C(NC(C2=CC(=CC=C12)Cl)C1=C(C=CC=C1)F)=O Chemical compound C(C)OCCN1C(NC(C2=CC(=CC=C12)Cl)C1=C(C=CC=C1)F)=O NYQWTGSPKJLMIH-UHFFFAOYSA-N 0.000 description 1
- SEKFTHLXFSORKJ-UHFFFAOYSA-N CS(C(C=C1C(C2=CC=CC=C2)N2)=CC=C1N(CC1CC1)C2=O)(=O)=O Chemical compound CS(C(C=C1C(C2=CC=CC=C2)N2)=CC=C1N(CC1CC1)C2=O)(=O)=O SEKFTHLXFSORKJ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 231100000456 subacute toxicity Toxicity 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D239/80—Oxygen atoms
- C07D239/82—Oxygen atoms with an aryl radical attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11833270A JPS4834598B1 (enrdf_load_stackoverflow) | 1970-12-23 | 1970-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH563995A5 true CH563995A5 (en) | 1975-07-15 |
Family
ID=14734027
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH35875A CH563995A5 (en) | 1970-12-23 | 1971-07-12 | 3, 4- dihydro-2 (1h)-quin azolinones - anti-inflammatories and analge |
| CH35775A CH564539A5 (enrdf_load_stackoverflow) | 1970-12-23 | 1971-07-12 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH35775A CH564539A5 (enrdf_load_stackoverflow) | 1970-12-23 | 1971-07-12 |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS4834598B1 (enrdf_load_stackoverflow) |
| AT (2) | AT310177B (enrdf_load_stackoverflow) |
| CH (2) | CH563995A5 (enrdf_load_stackoverflow) |
| CS (2) | CS181693B2 (enrdf_load_stackoverflow) |
| ES (2) | ES419266A1 (enrdf_load_stackoverflow) |
| SU (1) | SU475774A3 (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2347506C (en) * | 1998-10-16 | 2009-06-23 | Sumitomo Pharmaceuticals Co., Ltd. | Quinazolinone derivatives |
-
1970
- 1970-12-23 JP JP11833270A patent/JPS4834598B1/ja active Pending
-
1971
- 1971-06-12 SU SU1754058A patent/SU475774A3/ru active
- 1971-07-12 CH CH35875A patent/CH563995A5/de not_active IP Right Cessation
- 1971-07-12 AT AT898372A patent/AT310177B/de active
- 1971-07-12 CH CH35775A patent/CH564539A5/xx not_active IP Right Cessation
- 1971-07-12 CS CS782975A patent/CS181693B2/cs unknown
- 1971-07-12 CS CS509771A patent/CS181665B2/cs unknown
- 1971-07-12 AT AT898472A patent/AT310178B/de active
-
1973
- 1973-10-02 ES ES419266A patent/ES419266A1/es not_active Expired
- 1973-10-02 ES ES419267A patent/ES419267A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT310178B (de) | 1973-09-25 |
| ES419266A1 (es) | 1977-01-01 |
| ES419267A1 (es) | 1976-11-01 |
| SU439980A3 (ru) | 1974-08-15 |
| AT310177B (de) | 1973-09-25 |
| CS181665B2 (en) | 1978-03-31 |
| CS181693B2 (en) | 1978-03-31 |
| JPS4834598B1 (enrdf_load_stackoverflow) | 1973-10-22 |
| SU475774A3 (ru) | 1975-06-30 |
| CH564539A5 (enrdf_load_stackoverflow) | 1975-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |