GB1156973A - Quinazoline Derivatives - Google Patents
Quinazoline DerivativesInfo
- Publication number
- GB1156973A GB1156973A GB29544/66A GB2954466A GB1156973A GB 1156973 A GB1156973 A GB 1156973A GB 29544/66 A GB29544/66 A GB 29544/66A GB 2954466 A GB2954466 A GB 2954466A GB 1156973 A GB1156973 A GB 1156973A
- Authority
- GB
- United Kingdom
- Prior art keywords
- piperazinyl
- alkyl
- carbon atoms
- quinazolines
- reacting
- 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
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title 1
- -1 substituted-phenyl Chemical group 0.000 abstract 38
- 125000004432 carbon atom Chemical group C* 0.000 abstract 14
- 125000000217 alkyl group Chemical group 0.000 abstract 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 9
- 238000006243 chemical reaction Methods 0.000 abstract 7
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 229910021529 ammonia Inorganic materials 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 150000002431 hydrogen Chemical class 0.000 abstract 3
- 150000003246 quinazolines Chemical class 0.000 abstract 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 230000029936 alkylation Effects 0.000 abstract 2
- 238000005804 alkylation reaction Methods 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000002357 guanidines Chemical class 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([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
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 abstract 1
- ZHSXQCFBOVNWGW-UHFFFAOYSA-N 2,4-dichloro-6,7-dipentoxyquinazoline Chemical compound ClC1=NC2=CC(=C(C=C2C(=N1)Cl)OCCCCC)OCCCCC ZHSXQCFBOVNWGW-UHFFFAOYSA-N 0.000 abstract 1
- NAABCYXBTAMFRP-UHFFFAOYSA-N 2,4-dichloro-6-methoxy-7-pentoxyquinazoline Chemical compound ClC1=NC2=CC(=C(C=C2C(=N1)Cl)OC)OCCCCC NAABCYXBTAMFRP-UHFFFAOYSA-N 0.000 abstract 1
- SYZWDBZZSFPIRY-UHFFFAOYSA-N 2-(carbamoylamino)-4,5-dipentoxybenzamide Chemical compound N(C(=O)N)C1=C(C(=O)N)C=C(C(=C1)OCCCCC)OCCCCC SYZWDBZZSFPIRY-UHFFFAOYSA-N 0.000 abstract 1
- YAXKLRNDGNTYSS-UHFFFAOYSA-N 2-(carbamoylamino)-5-methoxy-4-pentoxybenzamide Chemical compound CCCCCOC1=CC(NC(N)=O)=C(C=C1OC)C(N)=O YAXKLRNDGNTYSS-UHFFFAOYSA-N 0.000 abstract 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 abstract 1
- YUNDARGCSSKMAB-UHFFFAOYSA-N 2-amino-5-methoxy-4-pentoxybenzamide Chemical compound C(CCCC)OC=1C=C(C(C(=O)N)=CC1OC)N YUNDARGCSSKMAB-UHFFFAOYSA-N 0.000 abstract 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 abstract 1
- KPEKTRARZLEBCG-UHFFFAOYSA-N 2-methylpropyl piperazine-1-carboxylate Chemical compound CC(C)COC(=O)N1CCNCC1 KPEKTRARZLEBCG-UHFFFAOYSA-N 0.000 abstract 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 abstract 1
- KWNQIIMVPSMYEM-UHFFFAOYSA-N 6,7-dimethoxy-1h-quinazoline-2,4-dione Chemical compound N1C(=O)NC(=O)C2=C1C=C(OC)C(OC)=C2 KWNQIIMVPSMYEM-UHFFFAOYSA-N 0.000 abstract 1
- NOCHXMQWTMBHCC-UHFFFAOYSA-N 6,7-dimethoxy-1h-quinazoline-2,4-dithione Chemical compound N1C(=S)NC(=S)C2=C1C=C(OC)C(OC)=C2 NOCHXMQWTMBHCC-UHFFFAOYSA-N 0.000 abstract 1
- WGTZVPKTBFWJFB-UHFFFAOYSA-N 6,7-dimethoxy-2,4-bis(methylsulfanyl)quinazoline Chemical compound CSC1=NC(SC)=C2C=C(OC)C(OC)=CC2=N1 WGTZVPKTBFWJFB-UHFFFAOYSA-N 0.000 abstract 1
- GXLPMEUYBFWKLS-UHFFFAOYSA-N 6,7-dimethoxy-2-methylsulfanylquinazolin-4-amine Chemical compound CSC1=NC(N)=C2C=C(OC)C(OC)=CC2=N1 GXLPMEUYBFWKLS-UHFFFAOYSA-N 0.000 abstract 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 abstract 1
- 125000005530 alkylenedioxy group Chemical group 0.000 abstract 1
- 238000006254 arylation reaction Methods 0.000 abstract 1
- 125000005605 benzo group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 238000005574 benzylation reaction Methods 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 125000004799 bromophenyl group Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000000068 chlorophenyl group Chemical group 0.000 abstract 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 abstract 1
- 125000004188 dichlorophenyl group Chemical group 0.000 abstract 1
- 125000004212 difluorophenyl group Chemical group 0.000 abstract 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 abstract 1
- 125000001207 fluorophenyl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- 125000005394 methallyl group Chemical group 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 abstract 1
- 238000006177 thiolation reaction Methods 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
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46987965A | 1965-07-06 | 1965-07-06 | |
| US55570466A | 1966-06-07 | 1966-06-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1156973A true GB1156973A (en) | 1969-07-02 |
Family
ID=27042885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB29544/66A Expired GB1156973A (en) | 1965-07-06 | 1966-06-30 | Quinazoline Derivatives |
Country Status (11)
| Country | Link |
|---|---|
| AT (3) | AT289122B (forum.php) |
| BE (1) | BE683741A (forum.php) |
| CH (1) | CH473130A (forum.php) |
| DE (1) | DE1620138C3 (forum.php) |
| DK (1) | DK127599B (forum.php) |
| ES (2) | ES328686A1 (forum.php) |
| FR (1) | FR6396M (forum.php) |
| GB (1) | GB1156973A (forum.php) |
| NO (1) | NO119278B (forum.php) |
| SE (1) | SE342454B (forum.php) |
| SG (1) | SG12672G (forum.php) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2120495A1 (de) * | 1970-05-21 | 1971-12-02 | Pfizer Inc., New York, N.Y. (V.St.A.) | Neue Trialkoxychinazolin-Verbindungen und Verfahren zu ihrer Herstellung |
| DE2530894A1 (de) * | 1974-07-25 | 1976-02-05 | Pfizer | Chinanzolinderivate |
| GB2142625A (en) * | 1983-06-01 | 1985-01-23 | Spofa Spojene Podniky | Piperazino-quinazolines |
| WO1994005628A1 (en) | 1992-08-31 | 1994-03-17 | Acic (Canada) Inc. | Synthesis of 2-substituted quinazoline compounds (such as terazosin) and meobentine and bethanidine and intermediates therefor |
| LT3038B (en) | 1992-02-25 | 1994-09-25 | Recordati Chem Pharm | Heterobicyclic compounds |
| US5753641A (en) * | 1991-03-20 | 1998-05-19 | Merck & Co., Inc. | Method of treatment for benign prostatic hyperplasia |
| WO2003055866A1 (en) * | 2001-12-21 | 2003-07-10 | Bayer Pharmaceuticals Corporation | Quinazoline and quinoline derivative compounds as inhibitors of prolylpeptidase, inducers of apoptosis and cancer treatment agents |
| JPWO2017150174A1 (ja) * | 2016-03-04 | 2019-06-13 | 株式会社 シンスター・ジャパン | ２，４−ジアミノキナゾリン誘導体又はその塩を有効成分として含有する医薬品組成物、及び、特定の構造を有する２，４−ジアミノキナゾリン誘導体 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK159079A (da) * | 1978-05-18 | 1979-11-19 | Pfizer | Fremgangsmaade til fremstilling af derivater af 4-amino-2-piperidinoquinazolin eller syreadditionssalte deraf |
| FI79107C (fi) * | 1984-06-25 | 1989-11-10 | Orion Yhtymae Oy | Foerfarande foer framstaellning av stabil -form av prazosinhydroklorid. |
| RU2507199C1 (ru) * | 2012-09-10 | 2014-02-20 | Владимир Иванович Петров | Производные хиназолина, обладающие антидепрессивной, анксиолитической и ноотропной активностью |
| RU2507198C1 (ru) * | 2012-09-10 | 2014-02-20 | Владимир Иванович Петров | Производные хиназолина, обладающие ноотропной и антигипоксической активностью |
-
1966
- 1966-06-30 GB GB29544/66A patent/GB1156973A/en not_active Expired
- 1966-07-02 DE DE1966P0039852 patent/DE1620138C3/de not_active Expired
- 1966-07-05 AT AT641266A patent/AT289122B/de not_active IP Right Cessation
- 1966-07-05 AT AT193868A patent/AT289806B/de not_active IP Right Cessation
- 1966-07-05 CH CH974666A patent/CH473130A/fr not_active IP Right Cessation
- 1966-07-05 FR FR68199A patent/FR6396M/fr not_active Expired
- 1966-07-05 NO NO16379666A patent/NO119278B/no unknown
- 1966-07-05 AT AT1161769A patent/AT300814B/de not_active IP Right Cessation
- 1966-07-05 ES ES0328686A patent/ES328686A1/es not_active Expired
- 1966-07-06 DK DK351066A patent/DK127599B/da unknown
- 1966-07-06 SE SE928066A patent/SE342454B/xx unknown
- 1966-07-06 BE BE683741D patent/BE683741A/xx not_active IP Right Cessation
-
1967
- 1967-04-17 ES ES339406A patent/ES339406A1/es not_active Expired
-
1972
- 1972-12-31 SG SG12672A patent/SG12672G/en unknown
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2120495A1 (de) * | 1970-05-21 | 1971-12-02 | Pfizer Inc., New York, N.Y. (V.St.A.) | Neue Trialkoxychinazolin-Verbindungen und Verfahren zu ihrer Herstellung |
| DE2167157C2 (de) * | 1970-05-21 | 1982-06-09 | Pfizer Inc., 10017 New York, N.Y. | 4-Substituierte-2-halogen-6,7,8-trimethoxychinazoline |
| DE2530894A1 (de) * | 1974-07-25 | 1976-02-05 | Pfizer | Chinanzolinderivate |
| GB2142625A (en) * | 1983-06-01 | 1985-01-23 | Spofa Spojene Podniky | Piperazino-quinazolines |
| US6046183A (en) * | 1991-03-20 | 2000-04-04 | Merck & Co., Inc. | Method of synergistic treatment for benign prostatic hyperplasia |
| US5753641A (en) * | 1991-03-20 | 1998-05-19 | Merck & Co., Inc. | Method of treatment for benign prostatic hyperplasia |
| LT3038B (en) | 1992-02-25 | 1994-09-25 | Recordati Chem Pharm | Heterobicyclic compounds |
| US5675006A (en) * | 1992-08-31 | 1997-10-07 | Brantford Chemicals Inc. | Methods of making ureas and guanidines, including, terazosin, prazosin, doxazosin, tiodazosin, trimazosin, quinazosin, and bunazosin (exemplary of 2- substituted quinazoline compounds), and meobentine, and bethanidine and intermediates therefor |
| US5686612A (en) * | 1992-08-31 | 1997-11-11 | Brantford Chemicals Inc. | Methods of making ureas and guanidines, including terazosin, prazosin, doxazosin, tiodazosin, trimazosin, quinazosin, and bunazosin (exemplary of 2-substituted quinazoline compounds), and meobentine, and bethanidine and intermediates thereof |
| WO1994005628A1 (en) | 1992-08-31 | 1994-03-17 | Acic (Canada) Inc. | Synthesis of 2-substituted quinazoline compounds (such as terazosin) and meobentine and bethanidine and intermediates therefor |
| US6080860A (en) * | 1992-08-31 | 2000-06-27 | Brantford Chemicalss Inc. | Methods of making ureas and guanidines including, terazosin, prazosin, doxazosin, tiodazosin, trimazosin, quinazosin and bunazosin (exemplary of 2-substituted quinazoline compounds), and meobentine, and bethanidine and intermediates therefor |
| WO2003055866A1 (en) * | 2001-12-21 | 2003-07-10 | Bayer Pharmaceuticals Corporation | Quinazoline and quinoline derivative compounds as inhibitors of prolylpeptidase, inducers of apoptosis and cancer treatment agents |
| JPWO2017150174A1 (ja) * | 2016-03-04 | 2019-06-13 | 株式会社 シンスター・ジャパン | ２，４−ジアミノキナゾリン誘導体又はその塩を有効成分として含有する医薬品組成物、及び、特定の構造を有する２，４−ジアミノキナゾリン誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| AT289122B (de) | 1971-04-13 |
| AT300814B (de) | 1972-08-10 |
| DE1620138A1 (de) | 1970-03-12 |
| DK127599B (da) | 1973-12-03 |
| DE1620138C3 (de) | 1978-08-17 |
| SE342454B (forum.php) | 1972-02-07 |
| ES339406A1 (es) | 1968-07-16 |
| BE683741A (forum.php) | 1967-01-06 |
| NO119278B (forum.php) | 1970-04-27 |
| SG12672G (en) | 1988-09-02 |
| CH473130A (fr) | 1969-05-31 |
| ES328686A1 (es) | 1967-09-01 |
| FR6396M (forum.php) | 1968-10-21 |
| AT289806B (de) | 1971-05-10 |
| DE1620138B2 (de) | 1977-12-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 423P | Notice of intention to present a petition (sect. 23/1949) | ||
| 423P | Notice of intention to present a petition (sect. 23/1949) | ||
| EPO | Patent for which application for extension of term has been made to the comptroller or the court | ||
| EPF | Patent extended in pursuance of application for extension of term and in force | ||
| EPF | Patent extended in pursuance of application for extension of term and in force | ||
| PE20 | Patent expired after termination of 20 years |