LU84775A1 - Nouveaux derives cycloaliphatiques condenses de pyrido(1,2-a)pyrimidines substituees - Google Patents
Nouveaux derives cycloaliphatiques condenses de pyrido(1,2-a)pyrimidines substituees Download PDFInfo
- Publication number
- LU84775A1 LU84775A1 LU84775A LU84775A LU84775A1 LU 84775 A1 LU84775 A1 LU 84775A1 LU 84775 A LU84775 A LU 84775A LU 84775 A LU84775 A LU 84775A LU 84775 A1 LU84775 A1 LU 84775A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- pyrido
- benzylidene
- acid
- oxo
- tetrahydro
- Prior art date
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- 150000003230 pyrimidines Chemical class 0.000 title description 2
- -1 formyloxy Chemical group 0.000 claims description 145
- 150000001875 compounds Chemical class 0.000 claims description 113
- 239000002253 acid Substances 0.000 claims description 109
- UPGZAERNNNZSPM-UHFFFAOYSA-N quinazoline-8-carboxylic acid Chemical compound N1=CN=C2C(C(=O)O)=CC=CC2=C1 UPGZAERNNNZSPM-UHFFFAOYSA-N 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 36
- UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 claims description 8
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 230000003266 anti-allergic effect Effects 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- BQIKRTGTPBOIMK-UHFFFAOYSA-N [O]C[O] Chemical compound [O]C[O] BQIKRTGTPBOIMK-UHFFFAOYSA-N 0.000 claims description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 206010061459 Gastrointestinal ulcer Diseases 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000002547 new drug Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 35
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000002244 precipitate Substances 0.000 description 26
- 238000001914 filtration Methods 0.000 description 25
- 150000003254 radicals Chemical class 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 20
- 239000011734 sodium Substances 0.000 description 19
- 229910052708 sodium Inorganic materials 0.000 description 19
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
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- 238000000034 method Methods 0.000 description 10
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- 238000000354 decomposition reaction Methods 0.000 description 9
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical group C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 7
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
- LBMGFLVZIOZDHZ-UHFFFAOYSA-N 4h-pyrido[1,2-a]pyrimidine-7-carboxylic acid Chemical compound C1C=CN=C2C=CC(C(=O)O)=CN21 LBMGFLVZIOZDHZ-UHFFFAOYSA-N 0.000 description 6
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- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
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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
- C07D471/02—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 two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8212429 | 1982-04-29 | ||
| GB8212429 | 1982-04-29 | ||
| GB8309259 | 1983-04-06 | ||
| GB838309259A GB8309259D0 (en) | 1983-04-06 | 1983-04-06 | Condensed cycloaliphatic derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU84775A1 true LU84775A1 (fr) | 1983-11-17 |
Family
ID=26282687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU84775A LU84775A1 (fr) | 1982-04-29 | 1983-04-27 | Nouveaux derives cycloaliphatiques condenses de pyrido(1,2-a)pyrimidines substituees |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4521419A (enExample) |
| AT (1) | AT384808B (enExample) |
| AU (1) | AU557703B2 (enExample) |
| CA (1) | CA1192548A (enExample) |
| CH (1) | CH660485A5 (enExample) |
| CS (1) | CS233748B2 (enExample) |
| DE (1) | DE3315299A1 (enExample) |
| DK (1) | DK192683A (enExample) |
| ES (1) | ES8406476A1 (enExample) |
| FI (1) | FI74467C (enExample) |
| FR (1) | FR2526020B1 (enExample) |
| GR (1) | GR78546B (enExample) |
| HU (1) | HU188274B (enExample) |
| IL (1) | IL68505A (enExample) |
| IT (1) | IT1194215B (enExample) |
| LU (1) | LU84775A1 (enExample) |
| NL (1) | NL8301505A (enExample) |
| NO (1) | NO831503L (enExample) |
| NZ (1) | NZ204041A (enExample) |
| PH (1) | PH18388A (enExample) |
| PT (1) | PT76609B (enExample) |
| SE (1) | SE8302411L (enExample) |
| YU (1) | YU95583A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63183581A (ja) * | 1985-10-03 | 1988-07-28 | Tokyo Tanabe Co Ltd | ピリド〔１，２−ａ〕ピリミジン誘導体、その製造法及びそれを有効成分とするアレルギ−疾患治療薬 |
| CN112321465B (zh) * | 2019-07-18 | 2023-06-06 | 上海现代药物制剂工程研究中心有限公司 | 一种含苯基化合物、其中间体、制备方法及应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3965100A (en) * | 1975-02-26 | 1976-06-22 | E. R. Squibb & Sons, Inc. | 2,3-Dihydrocyclopenta[d]pyrido[1,2-a]pyrimidin-10(1H)-one and its derivatives |
| US3935197A (en) * | 1975-05-16 | 1976-01-27 | E. R. Squibb & Sons, Inc. | 2-Styryl-4H-pyrido(1,2-a)pyrimidin-4-ones |
| US4033961A (en) * | 1975-10-07 | 1977-07-05 | Warner-Lambert Company | Pyrido[2-1-b]quinazolin-ones and their methods of preparation |
| DE2557425C2 (de) * | 1975-12-19 | 1987-03-19 | C.H. Boehringer Sohn, 6507 Ingelheim | 11-Oxo-11-H-pyrido[2,1-b]-chinazolin-2-carbonsäure und ihre Salze, Verfahren zu ihrer Herstellung und Arzneimittel |
| HU174693B (hu) * | 1976-02-12 | 1980-03-28 | Chinoin Gyogyszer Es Vegyeszet | Sposob poluchenija kondensirovannykh proizvodnykh pirimidina |
| US4066767A (en) * | 1976-11-01 | 1978-01-03 | Warner-Lambert Company | 8-(1H-Tetrazol-5-yl)-11H-pyrido[2,1-b]quinazolin-11-ones and method of treating bronchial asthma using them |
| HU182009B (en) * | 1977-08-19 | 1983-12-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing substituted pirido-square bracket-1,2-a-square bracket closed-pyrimidines, pyrrolo-square bracket-1,2-a-square bracket closed-pyrimidines |
| AU527931B2 (en) * | 1979-05-08 | 1983-03-31 | Farmitalia Carlo Erba S.P.A. | Substituted pyrido(1,2-a)pyrimidines |
| AT377586B (de) * | 1981-06-30 | 1985-04-10 | Erba Farmitalia | Verfahren zur herstellung von substituierten pyrrolo-(2,1-b)-chinazolinen und pyrido(2,1-b)chinazolinen |
-
1983
- 1983-04-22 ES ES521739A patent/ES8406476A1/es not_active Expired
- 1983-04-26 FI FI831426A patent/FI74467C/fi not_active IP Right Cessation
- 1983-04-26 IT IT20779/83A patent/IT1194215B/it active
- 1983-04-26 GR GR71210A patent/GR78546B/el unknown
- 1983-04-27 YU YU00955/83A patent/YU95583A/xx unknown
- 1983-04-27 HU HU831451A patent/HU188274B/hu not_active IP Right Cessation
- 1983-04-27 AU AU13991/83A patent/AU557703B2/en not_active Ceased
- 1983-04-27 LU LU84775A patent/LU84775A1/fr unknown
- 1983-04-27 DE DE19833315299 patent/DE3315299A1/de not_active Withdrawn
- 1983-04-27 IL IL68505A patent/IL68505A/xx unknown
- 1983-04-27 US US06/489,057 patent/US4521419A/en not_active Expired - Fee Related
- 1983-04-27 PH PH28824A patent/PH18388A/en unknown
- 1983-04-28 CS CS833005A patent/CS233748B2/cs unknown
- 1983-04-28 CH CH2286/83A patent/CH660485A5/de not_active IP Right Cessation
- 1983-04-28 FR FR8307052A patent/FR2526020B1/fr not_active Expired
- 1983-04-28 AT AT0154883A patent/AT384808B/de not_active IP Right Cessation
- 1983-04-28 SE SE8302411A patent/SE8302411L/xx not_active Application Discontinuation
- 1983-04-28 DK DK192683A patent/DK192683A/da not_active Application Discontinuation
- 1983-04-28 NO NO831503A patent/NO831503L/no unknown
- 1983-04-28 NL NL8301505A patent/NL8301505A/nl not_active Application Discontinuation
- 1983-04-28 CA CA000426896A patent/CA1192548A/en not_active Expired
- 1983-04-28 PT PT76609A patent/PT76609B/pt unknown
- 1983-04-28 NZ NZ204041A patent/NZ204041A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2526020B1 (fr) | 1986-03-21 |
| SE8302411L (sv) | 1983-10-30 |
| PH18388A (en) | 1985-06-19 |
| US4521419A (en) | 1985-06-04 |
| NZ204041A (en) | 1985-02-28 |
| IL68505A0 (en) | 1983-07-31 |
| AT384808B (de) | 1988-01-11 |
| DK192683A (da) | 1983-10-30 |
| ES521739A0 (es) | 1984-07-01 |
| GR78546B (enExample) | 1984-09-27 |
| PT76609B (en) | 1986-01-17 |
| FI831426A0 (fi) | 1983-04-26 |
| ATA154883A (de) | 1987-06-15 |
| FI74467B (fi) | 1987-10-30 |
| FI831426L (fi) | 1983-10-30 |
| DK192683D0 (da) | 1983-04-28 |
| IT1194215B (it) | 1988-09-14 |
| FR2526020A1 (fr) | 1983-11-04 |
| IT8320779A0 (it) | 1983-04-26 |
| HU188274B (en) | 1986-03-28 |
| NO831503L (no) | 1983-10-31 |
| CH660485A5 (de) | 1987-04-30 |
| DE3315299A1 (de) | 1983-11-03 |
| FI74467C (fi) | 1988-02-08 |
| YU95583A (en) | 1986-12-31 |
| ES8406476A1 (es) | 1984-07-01 |
| NL8301505A (nl) | 1983-11-16 |
| CS233748B2 (en) | 1985-03-14 |
| IT8320779A1 (it) | 1984-10-26 |
| IL68505A (en) | 1986-01-31 |
| CA1192548A (en) | 1985-08-27 |
| SE8302411D0 (sv) | 1983-04-28 |
| PT76609A (en) | 1983-05-01 |
| AU1399183A (en) | 1983-11-03 |
| AU557703B2 (en) | 1987-01-08 |
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