GB1185524A - Quinazolinone Derivatives - Google Patents
Quinazolinone DerivativesInfo
- Publication number
- GB1185524A GB1185524A GB27226/67A GB2722667A GB1185524A GB 1185524 A GB1185524 A GB 1185524A GB 27226/67 A GB27226/67 A GB 27226/67A GB 2722667 A GB2722667 A GB 2722667A GB 1185524 A GB1185524 A GB 1185524A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- contacting
- methyl
- formula
- halogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 title abstract 2
- -1 methoxy benzyloxy Chemical group 0.000 abstract 8
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical class [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 229940035676 analgesics Drugs 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 239000002220 antihypertensive agent Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000012954 diazonium Substances 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000003944 tolyl group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/80—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,185,524. Quinazolinone derivatives. G. D. SEARLE & CO. 13 June, 1967 [14 June, 1966], No. 27226/67. Heading C2C. Novel compounds of Formula I and non toxic acid addition salts thereof wherein X is a hydrogen atom, a methyl or methoxy radical or a halogen atom, Y, Y<SP>1</SP> and Y<SP>11</SP> are each a hydrogen or halogen atom, a methyl, methoxy benzyloxy, trifluoromethyl or hydroxy radical where at least two of the substituents represented by Y, Y<SP>1</SP> and Y<SP>11</SP> are identical; alk is a C 1-6 alkylene radical separating the nitrogen atoms attached thereto by at least 2 carbon atoms and NRR<SP>1</SP> is a disubstituted amino radical wherein R is a C 1-6 alkyl group and R<SP>1</SP> is a C 1-6 alkyl group or a benzyl radical or NRR<SP>1</SP> is a 1-pyrrolidinyl, piperidino, morpholino or a 4 R<SP>11</SP> substituted 1- piperazinyl radical where R<SP>11</SP> is a methyl, phenyl, tolyl or halophenyl radical are prepared (a) by contacting the corresponding 1-hydroquinazoline derivative with a halide of RR<SP>1</SP>N- alk-halogen in the presence of a strong base, (b) by contacting the corresponding 1-haloalkyl-quinazoline derivative with an amine of formula HNRR<SP>1</SP> or (c) when a compound is desired wherein Y, Y<SP>1</SP> and Y<SP>11</SP> are hydrogen atoms by contacting the corresponding 3- hydro-quinazoline derivative which is substituted in the 1-position by a dialkylaminoalkyl radical with an aromatic halide of formula C 6 H 5 -Z-halogen, where Z is a diazonium or phenyliodonium radical in the presence of a strong base. The compounds of the invention possess activity as analgesics, hypotensive agents, antiinflammatory agents and antibiotics.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR110072A FR6720M (en) | 1967-06-13 | 1967-06-13 | |
| US728330A US3528982A (en) | 1967-06-13 | 1968-05-10 | N-dialkylaminoalkyl-3,4-dihydro-2(1h)-quinazolinones |
| CH856568A CH492728A (en) | 1967-06-13 | 1968-06-10 | Process for the preparation of derivatives of cycloalkanespiro-5 oxazolidines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55737166A | 1966-06-14 | 1966-06-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1185524A true GB1185524A (en) | 1970-03-25 |
Family
ID=24225124
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27226/67A Expired GB1185524A (en) | 1966-06-14 | 1967-06-13 | Quinazolinone Derivatives |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE699924A (en) |
| DE (1) | DE1695735A1 (en) |
| FR (1) | FR6549M (en) |
| GB (1) | GB1185524A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2803298A1 (en) * | 1999-12-30 | 2001-07-06 | Adir | NOVEL LINEAR OR CYCLIC UREAS, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
-
1967
- 1967-06-13 DE DE19671695735 patent/DE1695735A1/en active Pending
- 1967-06-13 GB GB27226/67A patent/GB1185524A/en not_active Expired
- 1967-06-14 FR FR110314A patent/FR6549M/fr not_active Expired
- 1967-06-14 BE BE699924D patent/BE699924A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2803298A1 (en) * | 1999-12-30 | 2001-07-06 | Adir | NOVEL LINEAR OR CYCLIC UREAS, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1695735A1 (en) | 1971-04-22 |
| FR6549M (en) | 1968-12-16 |
| BE699924A (en) | 1967-12-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |