PH27040A - Substituted imidazole (2-Ib) quinazolin 5(3H)-ones and related tricyclic compounds - Google Patents
Substituted imidazole (2-Ib) quinazolin 5(3H)-ones and related tricyclic compounds Download PDFInfo
- Publication number
- PH27040A PH27040A PH39276A PH39276A PH27040A PH 27040 A PH27040 A PH 27040A PH 39276 A PH39276 A PH 39276A PH 39276 A PH39276 A PH 39276A PH 27040 A PH27040 A PH 27040A
- Authority
- PH
- Philippines
- Prior art keywords
- compound
- imidazo
- compounds
- quinazolin
- morpholinyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 39
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title abstract 3
- FHBBETAOBPMWTJ-UHFFFAOYSA-N 1h-quinazolin-5-one Chemical class N1C=NC=C2C(=O)C=CC=C21 FHBBETAOBPMWTJ-UHFFFAOYSA-N 0.000 title 1
- 150000002460 imidazoles Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims 2
- 241000448280 Elates Species 0.000 claims 1
- 239000011717 all-trans-retinol Substances 0.000 claims 1
- 235000019169 all-trans-retinol Nutrition 0.000 claims 1
- -1 1-substituted-2-methyl-2-imidazoline Chemical class 0.000 abstract description 7
- 150000003839 salts Chemical class 0.000 abstract description 6
- 229940124630 bronchodilator Drugs 0.000 abstract description 3
- 239000000168 bronchodilator agent Substances 0.000 abstract description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- 238000000034 method Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 241000124008 Mammalia Species 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000003182 bronchodilatating effect Effects 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 208000009079 Bronchial Spasm Diseases 0.000 description 2
- 206010006482 Bronchospasm Diseases 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000206607 Porphyra umbilicalis Species 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 239000007928 intraperitoneal injection Substances 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 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 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
- 241000272522 Anas Species 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010010071 Coma Diseases 0.000 description 1
- 101000939348 Homo sapiens NEDD8-activating enzyme E1 regulatory subunit Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 102100029781 NEDD8-activating enzyme E1 regulatory subunit Human genes 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- YEJAJYAHJQIWNU-UHFFFAOYSA-N azelastine hydrochloride Chemical compound Cl.C1CN(C)CCCC1N1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 YEJAJYAHJQIWNU-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 230000007883 bronchodilation Effects 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
- 239000007963 capsule composition Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007911 effervescent powder Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000009950 felting Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N hydroxymaleic acid group Chemical group O/C(/C(=O)O)=C/C(=O)O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 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
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- MKQLBNJQQZRQJU-UHFFFAOYSA-N morpholin-4-amine Chemical compound NN1CCOCC1 MKQLBNJQQZRQJU-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 210000005092 tracheal tissue Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Lubricants (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Detergent Compositions (AREA)
- Luminescent Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/247,797 US4871732A (en) | 1988-09-22 | 1988-09-22 | Substituted imidazo(2,1-b)quinazolin-5(3H)-ones and related tricyclic compounds and use as bronchodilators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH27040A true PH27040A (en) | 1993-02-01 |
Family
ID=22936415
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH39276A PH27040A (en) | 1988-09-22 | 1989-09-22 | Substituted imidazole (2-Ib) quinazolin 5(3H)-ones and related tricyclic compounds |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4871732A (fr) |
| EP (1) | EP0360261B1 (fr) |
| JP (1) | JP2942572B2 (fr) |
| KR (1) | KR0144866B1 (fr) |
| CN (1) | CN1041364A (fr) |
| AT (1) | ATE96439T1 (fr) |
| AU (1) | AU610816B2 (fr) |
| CA (1) | CA1334294C (fr) |
| DE (1) | DE68910253T2 (fr) |
| DK (1) | DK466089A (fr) |
| ES (1) | ES2061860T3 (fr) |
| FI (1) | FI89601C (fr) |
| HU (1) | HU201938B (fr) |
| IL (1) | IL91699A0 (fr) |
| NO (1) | NO168709C (fr) |
| NZ (1) | NZ230704A (fr) |
| PH (1) | PH27040A (fr) |
| PT (1) | PT91771B (fr) |
| ZA (1) | ZA897106B (fr) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2008998A1 (en) * | 1970-02-26 | 1971-09-16 | Imidazo-(2,1-b)-quinazolines cns active | |
| US3875161A (en) * | 1971-07-15 | 1975-04-01 | Sandoz Ag | Imidazo(2,1-b)quinazolin-5(1OH)-ones |
| NL7314532A (fr) * | 1972-10-27 | 1974-05-01 | ||
| DE3220438A1 (de) * | 1982-05-29 | 1983-12-01 | Troponwerke GmbH & Co KG, 5000 Köln | Chinazolinonderivate, verfahren zu ihrer herstellung und ihre verwendung inn arzneimitteln |
| AU5865686A (en) * | 1985-05-01 | 1986-11-18 | Schering Corporation | Pyrimidine derivatives having anti-allergy anti-inflammatory and immuno suppressant activity |
-
1988
- 1988-09-22 US US07/247,797 patent/US4871732A/en not_active Expired - Fee Related
-
1989
- 1989-09-18 AU AU41525/89A patent/AU610816B2/en not_active Ceased
- 1989-09-18 ZA ZA897106A patent/ZA897106B/xx unknown
- 1989-09-19 NZ NZ230704A patent/NZ230704A/en unknown
- 1989-09-19 CA CA000612007A patent/CA1334294C/fr not_active Expired - Fee Related
- 1989-09-20 FI FI894458A patent/FI89601C/fi not_active IP Right Cessation
- 1989-09-20 IL IL91699A patent/IL91699A0/xx not_active IP Right Cessation
- 1989-09-21 KR KR1019890013572A patent/KR0144866B1/ko not_active IP Right Cessation
- 1989-09-21 DK DK466089A patent/DK466089A/da not_active Application Discontinuation
- 1989-09-21 NO NO893762A patent/NO168709C/no unknown
- 1989-09-21 CN CN89107403A patent/CN1041364A/zh active Pending
- 1989-09-21 DE DE89117448T patent/DE68910253T2/de not_active Expired - Fee Related
- 1989-09-21 JP JP1243563A patent/JP2942572B2/ja not_active Expired - Fee Related
- 1989-09-21 HU HU894917A patent/HU201938B/hu not_active IP Right Cessation
- 1989-09-21 AT AT89117448T patent/ATE96439T1/de not_active IP Right Cessation
- 1989-09-21 EP EP89117448A patent/EP0360261B1/fr not_active Expired - Lifetime
- 1989-09-21 ES ES89117448T patent/ES2061860T3/es not_active Expired - Lifetime
- 1989-09-21 PT PT91771A patent/PT91771B/pt not_active IP Right Cessation
- 1989-09-22 PH PH39276A patent/PH27040A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK466089D0 (da) | 1989-09-21 |
| IL91699A0 (en) | 1990-06-10 |
| KR900004734A (ko) | 1990-04-12 |
| CN1041364A (zh) | 1990-04-18 |
| FI894458A0 (fi) | 1989-09-20 |
| DE68910253T2 (de) | 1994-02-24 |
| AU4152589A (en) | 1990-03-29 |
| PT91771A (pt) | 1990-03-30 |
| NO893762L (no) | 1990-03-23 |
| NO893762D0 (no) | 1989-09-21 |
| JPH02191277A (ja) | 1990-07-27 |
| NZ230704A (en) | 1991-03-26 |
| PT91771B (pt) | 1995-05-31 |
| ATE96439T1 (de) | 1993-11-15 |
| NO168709C (no) | 1992-03-25 |
| FI894458A (fi) | 1990-03-23 |
| US4871732A (en) | 1989-10-03 |
| HUT53104A (en) | 1990-09-28 |
| DE68910253D1 (de) | 1993-12-02 |
| NO168709B (no) | 1991-12-16 |
| KR0144866B1 (ko) | 1998-07-15 |
| ZA897106B (en) | 1990-06-27 |
| AU610816B2 (en) | 1991-05-23 |
| FI89601C (fi) | 1993-10-25 |
| JP2942572B2 (ja) | 1999-08-30 |
| FI89601B (fi) | 1993-07-15 |
| EP0360261B1 (fr) | 1993-10-27 |
| HU201938B (en) | 1991-01-28 |
| EP0360261A1 (fr) | 1990-03-28 |
| ES2061860T3 (es) | 1994-12-16 |
| DK466089A (da) | 1990-03-23 |
| CA1334294C (fr) | 1995-02-07 |
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