FI73435B - Foerfarande foer framstaellning av terapeutiskt anvaendbara nya 1,2,4-triazolo/4,3-a/kinazolin-5(4h)-oner och deras salter. - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara nya 1,2,4-triazolo/4,3-a/kinazolin-5(4h)-oner och deras salter. Download PDFInfo
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- FI73435B FI73435B FI823278A FI823278A FI73435B FI 73435 B FI73435 B FI 73435B FI 823278 A FI823278 A FI 823278A FI 823278 A FI823278 A FI 823278A FI 73435 B FI73435 B FI 73435B
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- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims description 22
- 230000001225 therapeutic effect Effects 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 37
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 239000000543 intermediate Substances 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 109
- -1 2,6-dimethylpiperidino, 3,5-dimethylpiperidino Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 5
- 150000001266 acyl halides Chemical class 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 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 claims description 2
- 125000005505 thiomorpholino group Chemical group 0.000 claims description 2
- LTJCKJVQPRZVDG-UHFFFAOYSA-N 3h-[1,2,4]triazolo[4,3-a]quinazolin-5-one Chemical class C1=CC=C2C(O)=NC3=NN=CN3C2=C1 LTJCKJVQPRZVDG-UHFFFAOYSA-N 0.000 claims 1
- 241000251730 Chondrichthyes Species 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 6
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- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
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- 125000002618 bicyclic heterocycle group Chemical group 0.000 abstract 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
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- 238000002474 experimental method Methods 0.000 description 6
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- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 210000003019 respiratory muscle Anatomy 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 229940072690 valium Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- 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
- C07D239/96—Two oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Claims (3)
1. Förfarande för framställning av terapeutiskt användbara nya 1,2,4-triazolo/4,3-a7kinazolin-5(4H)-oner med 5 formeIn (I) Λ & 7=”\ 10 n\-^N (i) R-p | li Y O 15 väri R är en väte- eller halogenatom eller en alkylgrupp med 1- 3 kolatomer, Y är en 1 - 6 kolatomer innehällande alkylgrupp med rak eller förgrenad kedja, en alkenylgrupp med 2- 4 kolatomer, en fenylgrupp eller en bensylgrupp, B är 20 CH- I J gruppen -CH- eller en -(CH2) -alkylen, väri n är ett heltal Λ 1, 2 eller 3 och X är gruppen -N<^ , väri R^ och R2, vilka R2 25 kan vara lika eller olika, betecknar en 1 - 6 kolatomer inne-hällande alkylgrupp med rak eller förgrenad kedja, en cyklo-alkylgrupp med 3-6 kolatomer eller en piperidinoalkylgrupp eller R^ och R2 bildar tillsammans med den kväveatom som de är bundna vid en pyrrolidinyl-, piperidino-, 2,3,4,5,6,7-30 hexahydroazepino-, 3-azabicyklo£3,2,2jnonano-, 2,6-dimetyl-piperidino-, 3,5-dimetylpiperidino-, morfolino- eller tio-morfolino eller en piperazin-l-ylgrupp, vilken kan vara substituerad med en alkylgrupp med 1-3 kolatomer, en fenylgrupp, en bensylgrupp eller en alkoxikarbonylgrupp med 2-5 35 kolatomer i alkoxidelen eller X är gruppen ^NH2 · C1 θ nh2 33 734 35 eller gruppen ' ° n -> u H Φ /.N "· -S-e Cl Θ ,
5. J H och deras syraadditionssalter, kännetecknat därav, att en förening med formeln (II) 10 • ,m2 / N . N R---------- j I (11) -- -- , N 15 "" Τ' N ib O väri R och Y har ovan angiven betydelse, omsätts med en halogenerad förening av en acylhalogenid med formeln (III)
20 Hal-B-CO-Hal1 (III) väri B har ovan angiven betydelse och Hal och Hal^ betecknar en klor- eller bromatom, för erhällande av en förening med formeln (II ) a 25 H NH-CO-B-Hal • / - N ... 30. il' I I «“a» X N y O väri R, Y, B och Hai har ovan angiven betydelse, varefter 35 föreningen (II ) cykliseras utan isolering eller först isoleras och sedan cykliseras, för erhällande av en förening med formeln (IV)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8128875 | 1981-09-24 | ||
| GB8128875 | 1981-09-24 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI823278A0 FI823278A0 (fi) | 1982-09-23 |
| FI823278L FI823278L (fi) | 1983-03-25 |
| FI73435B true FI73435B (fi) | 1987-06-30 |
| FI73435C FI73435C (sv) | 1987-10-09 |
Family
ID=10524710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI823278A FI73435C (sv) | 1981-09-24 | 1982-09-23 | Förfarande för framställning av terapeutiskt användbara nya 1,2,4-tria zolo/4,3-a/kinazolin-5(4H)-oner och deras salter. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4472400A (sv) |
| EP (1) | EP0076199B1 (sv) |
| JP (1) | JPS5865292A (sv) |
| AT (1) | ATE24509T1 (sv) |
| AU (1) | AU554959B2 (sv) |
| CA (1) | CA1193597A (sv) |
| DE (1) | DE3274860D1 (sv) |
| DK (1) | DK160308C (sv) |
| ES (1) | ES8400440A1 (sv) |
| FI (1) | FI73435C (sv) |
| GB (1) | GB2108495B (sv) |
| GR (1) | GR78044B (sv) |
| HU (1) | HU186975B (sv) |
| IE (1) | IE53858B1 (sv) |
| IL (1) | IL66835A (sv) |
| MA (1) | MA19604A1 (sv) |
| PT (1) | PT75602B (sv) |
| ZA (1) | ZA826891B (sv) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5442062A (en) * | 1991-10-24 | 1995-08-15 | The Upjohn Company | Imidazole derivatives and pharmaceutical compositions containing the same |
| JP2828506B2 (ja) * | 1994-05-24 | 1998-11-25 | エフ・ホフマン−ラ ロシュ アーゲー | 三環式ジカルボニル誘導体 |
| US5756502A (en) * | 1994-08-08 | 1998-05-26 | Warner-Lambert Company | Quinazolinone derivatives as cholyecystokinin (CCK) ligands |
| US6897213B1 (en) | 1995-11-21 | 2005-05-24 | Warner-Lambert Company | Heterocycles as cholecystokinin (CCK) ligands |
| CN1149214C (zh) * | 1998-12-04 | 2004-05-12 | 东丽株式会社 | 三唑并衍生物和含有它们作为有效组分的趋化因子抑制剂 |
| FR2792938B1 (fr) | 1999-04-28 | 2001-07-06 | Warner Lambert Co | NOUVELLES 1-AMINO TRIAZOLO [4,3-a] QUINAZOLINE-5-ONES INHIBITRICES DE PHOSPHODIESTERASES IV |
| PA8539501A1 (es) | 2001-02-14 | 2002-09-30 | Warner Lambert Co | Compuestos triazolo como inhibidores de mmp |
| EP1285922A1 (en) | 2001-08-13 | 2003-02-26 | Warner-Lambert Company | 1-Alkyl or 1-cycloalkyltriazolo[4,3-a]quinazolin-5-ones as phosphodiesterase inhibitors |
| FR2832711B1 (fr) | 2001-11-26 | 2004-01-30 | Warner Lambert Co | Derives de triazolo [4,3-a] pyrido [2,3-d] pyrimidin-5-ones, compositions les contenant, procede de preparation et utilisation |
| CN1891704A (zh) * | 2005-07-08 | 2007-01-10 | 中国科学院上海药物研究所 | 一类二肽酶四抑制剂及其制备方法和用途 |
| CN115197225B (zh) * | 2021-09-03 | 2023-04-11 | 贵州大学 | 一种五元杂环并喹唑啉酮类化合物及其制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50116498A (sv) * | 1974-02-27 | 1975-09-11 | ||
| US4145419A (en) * | 1976-05-21 | 1979-03-20 | Roussel Uclaf | Novel imidazobenzoxazines |
| GB1596652A (en) * | 1977-01-20 | 1981-08-26 | Roussel Lab Ltd | Imidazo (1,2-a) quinoline-2-carboxylic acid and derivatives |
| GB1576077A (en) * | 1977-04-13 | 1980-10-01 | Roussel Lab Ltd | 4,5-dihydro-4-oxophyrrolo(1,2-)-quinoxaline-2-carboxylic acids and derivatives |
| SE444319B (sv) * | 1977-11-18 | 1986-04-07 | Roussel Uclaf | Nya imidazobensoxazinderivat, forfarande for framstellning derav och farmaceutiska kompositioner innehallande dessa foreningar |
| SE439308B (sv) * | 1978-08-02 | 1985-06-10 | Roussel Uclaf | Imidazo(1,2-a)kinoxaliner och farmaceutiska kompositioner derav |
| DD139715A1 (de) * | 1978-09-29 | 1980-01-16 | Karl Kottke | Verfahren zur herstellung von 1-substituierten 4-aryl-s-triazolo(4,3-a)chinazolonen-(5) |
| FR2448541A1 (fr) * | 1979-02-09 | 1980-09-05 | Roussel Uclaf | Nouveaux derives de l'oxoimidazoquinoxaline et leurs sels, leur procede de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant |
| SE441449B (sv) * | 1979-02-09 | 1985-10-07 | Roussel Uclaf | Heterocykliska derivat och farmaceutiska kompositioner innehallande dessa derivat |
| ZA81708B (en) * | 1980-02-14 | 1982-06-30 | Roussel Uclaf | Triazoloquinazolinone derivatives |
-
1982
- 1982-09-17 IL IL66835A patent/IL66835A/xx unknown
- 1982-09-20 EP EP82401697A patent/EP0076199B1/fr not_active Expired
- 1982-09-20 AT AT82401697T patent/ATE24509T1/de not_active IP Right Cessation
- 1982-09-20 DE DE8282401697T patent/DE3274860D1/de not_active Expired
- 1982-09-20 ZA ZA826891A patent/ZA826891B/xx unknown
- 1982-09-21 US US06/420,798 patent/US4472400A/en not_active Expired - Fee Related
- 1982-09-22 DK DK420682A patent/DK160308C/da not_active IP Right Cessation
- 1982-09-22 AU AU88623/82A patent/AU554959B2/en not_active Ceased
- 1982-09-22 GR GR69335A patent/GR78044B/el unknown
- 1982-09-23 IE IE2310/82A patent/IE53858B1/en not_active IP Right Cessation
- 1982-09-23 PT PT75602A patent/PT75602B/pt not_active IP Right Cessation
- 1982-09-23 FI FI823278A patent/FI73435C/sv not_active IP Right Cessation
- 1982-09-23 MA MA19816A patent/MA19604A1/fr unknown
- 1982-09-23 GB GB08227126A patent/GB2108495B/en not_active Expired
- 1982-09-23 ES ES515904A patent/ES8400440A1/es not_active Expired
- 1982-09-23 CA CA000412016A patent/CA1193597A/fr not_active Expired
- 1982-09-24 HU HU823090A patent/HU186975B/hu not_active IP Right Cessation
- 1982-09-24 JP JP57165197A patent/JPS5865292A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IL66835A0 (en) | 1982-12-31 |
| PT75602B (fr) | 1985-12-09 |
| CA1193597A (fr) | 1985-09-17 |
| AU554959B2 (en) | 1986-09-11 |
| DK420682A (da) | 1983-03-25 |
| FI823278A0 (fi) | 1982-09-23 |
| IL66835A (en) | 1988-05-31 |
| ES515904A0 (es) | 1983-10-16 |
| FI823278L (fi) | 1983-03-25 |
| ES8400440A1 (es) | 1983-10-16 |
| DK160308B (da) | 1991-02-25 |
| ATE24509T1 (de) | 1987-01-15 |
| EP0076199B1 (fr) | 1986-12-30 |
| DE3274860D1 (en) | 1987-02-05 |
| US4472400A (en) | 1984-09-18 |
| JPS5865292A (ja) | 1983-04-18 |
| GB2108495A (en) | 1983-05-18 |
| FI73435C (sv) | 1987-10-09 |
| MA19604A1 (fr) | 1983-04-01 |
| GR78044B (sv) | 1984-09-26 |
| IE822310L (en) | 1983-03-24 |
| EP0076199A2 (fr) | 1983-04-06 |
| AU8862382A (en) | 1983-03-31 |
| JPH0322389B2 (sv) | 1991-03-26 |
| HU186975B (en) | 1985-10-28 |
| PT75602A (fr) | 1982-10-01 |
| ZA826891B (en) | 1983-10-26 |
| IE53858B1 (en) | 1989-03-29 |
| EP0076199A3 (en) | 1984-03-21 |
| DK160308C (da) | 1991-07-29 |
| GB2108495B (en) | 1985-07-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: ROUSSEL-UCLAF |