IE38393L - Derivatives of quinoline and related compounds. - Google Patents
Derivatives of quinoline and related compounds.Info
- Publication number
- IE38393L IE38393L IE731873A IE187373A IE38393L IE 38393 L IE38393 L IE 38393L IE 731873 A IE731873 A IE 731873A IE 187373 A IE187373 A IE 187373A IE 38393 L IE38393 L IE 38393L
- Authority
- IE
- Ireland
- Prior art keywords
- alkyl
- alkoxy
- reacting
- methyl
- aralkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 4
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 150000001408 amides Chemical class 0.000 abstract 4
- 229910004013 NO 2 Inorganic materials 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 150000004702 methyl esters Chemical class 0.000 abstract 2
- 150000002825 nitriles Chemical class 0.000 abstract 2
- NPCAVOFZVLVKDN-UHFFFAOYSA-N 2-(5,6,7,8-tetrahydroquinolin-2-yl)acetic acid Chemical compound C1CCCC2=NC(CC(=O)O)=CC=C21 NPCAVOFZVLVKDN-UHFFFAOYSA-N 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- -1 chloroformic acid ester Chemical class 0.000 abstract 1
- TXRCTTMWOSTRJB-UHFFFAOYSA-N dimethyl 3-methyl-6,7-dihydro-5H-quinoline-8,8-dicarboxylate Chemical compound CC=1C=NC=2C(CCCC2C1)(C(=O)OC)C(=O)OC TXRCTTMWOSTRJB-UHFFFAOYSA-N 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- MAIYBVDNQKEVTJ-UHFFFAOYSA-N methyl methanedithioate Chemical compound CSC=S MAIYBVDNQKEVTJ-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003222 pyridines Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 150000003556 thioamides Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1432378 Carbocyctic fused-ring pyridine derivatives JOHN WYETH & BRO Ltd 17 Sept 1973 [21 Oct 1972 15 Feb 1973 21 July 1973 16 Aug 1973] 48595/72 7424/73 34886/73 and 38701/73 Heading C2C [Also in Division A5] The invention comprises compounds of formula and their acid addition and (carboxylic) metal salts, wherein R<SP>1</SP>, R<SP>2</SP>, R<SP>6</SP> and R<SP>7</SP> are each H, CF 3 , alkyl, aralkyl or aryl, which radicals may be substituted (as appropriate) by alkyl, alkoxy, halogen, NO 2 or CF 3 , except that R<SP>7</SP> cannot itself be CF 3 , while additionally R<SP>1</SP>-R<SP>2</SP> may be -CH 2 -(CH 2 ) n -CH 2 - and R<SP>7</SP> may be more than one of the said substituents and may be present in the ring shown or in the ring formed when R<SP>1</SP>-R<SP>2</SP> is alkylene; X is CN, CONHR<SP>3</SP>, CSNHR<SP>3</SP> or CO 2 R<SP>5</SP>, where R<SP>3</SP> and R<SP>5</SP> are each H or alkyl (possibly substituted by alkoxy, Br, Cl, F, NO 2 or CF 3 ), or R<SP>5</SP> may be aralkyl or aryl, either possibly substituted by alkyl, alkoxy, halogen, NO 2 or CF 3 ; and m, n are each 1-3, but when R<SP>1</SP>-R<SP>2</SP> is alkylene, then m=n. In examples, these compounds are prepared as follows: (1) carloxylic acids and esters: by reacting an appropriate organo-Li compound (I : X=Li) with CO 2 or a chloroformic acid ester, or by esterifying acids or hydrolysing esters; (2) amides: by reacting a methyl ester with R<SP>3</SP>NH 2 or with HCONH 2 ; (3) nitriles: by dehydrating the amides with either P 2 S 5 /pyridine or PO(NMe 2 ) 3 ; (4) thioamides: by reacting (i) an amide with P 2 S 5 , or P 2 S 5 +H 2 S, (ii) a nitrile with H 2 S or MeCSNH 2 /HCl, or (iii) the methyl dithiocarboxylate (made from the lithium dithiocdrboxylate and MeI) with NH 3 . Starting materials of Formula I (X=H) and the by-products 5,6,7,8 - tetrahydroquinol - 2- ylacetic acid, its methyl ester and amide, and dimethyl 3 - methyl - 5,6,7,8 - tetrahydroquinoline-8,8-dicarboxylate, are also described.
[GB1432378A]
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4859572 | 1972-10-21 | ||
| GB742473*[A GB1432378A (en) | 1972-10-21 | 1973-02-15 | Fused carbocyclic ring derivatives of pyridine |
| GB3488673 | 1973-07-21 | ||
| GB3870173 | 1973-08-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE38393L true IE38393L (en) | 1974-04-21 |
| IE38393B1 IE38393B1 (en) | 1978-03-01 |
Family
ID=27447589
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1873/73A IE38393B1 (en) | 1972-10-21 | 1973-10-19 | Fused carbocyclic ring derivatives of pyridine |
Country Status (16)
| Country | Link |
|---|---|
| AR (1) | AR203377A1 (en) |
| AU (1) | AU474567B2 (en) |
| CA (1) | CA1011741A (en) |
| CH (3) | CH602648A5 (en) |
| CY (1) | CY996A (en) |
| DE (1) | DE2352585A1 (en) |
| FI (1) | FI52977C (en) |
| FR (1) | FR2203634B1 (en) |
| GB (1) | GB1432378A (en) |
| HK (1) | HK24479A (en) |
| IE (1) | IE38393B1 (en) |
| IN (1) | IN139235B (en) |
| KE (1) | KE2922A (en) |
| MY (1) | MY7900173A (en) |
| NL (1) | NL180213C (en) |
| PH (2) | PH12029A (en) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4085110A (en) * | 1972-10-21 | 1978-04-18 | John Wyeth & Brother, Ltd. | 1,2,3,5,6,7-Hexahydrodicyclopenta[b,e]pyridine derivatives |
| GB1463665A (en) * | 1973-11-26 | 1977-02-02 | Wyeth John & Brother Ltd | Preparation of fused ring pyridine derivatives and intermediates therefor |
| US4011228A (en) * | 1973-11-26 | 1977-03-08 | John Wyeth & Brother Limited | Carboxylic acid salts of tetrahydroquinolines and pyridine derivatives |
| GB1463666A (en) * | 1973-12-17 | 1977-02-02 | Wyeth John & Brother Ltd | Process for preparing fused carbocyclic ring derivatives of pyridine |
| GB1463667A (en) * | 1973-12-17 | 1977-02-02 | Wyeth John & Brother Ltd | Process for preparing thioamides |
| GB1561648A (en) | 1976-12-18 | 1980-02-27 | Wyeth John & Brother Ltd | Copper complexes of tetrahydroquinoline 8 - thiocarboxamides and related compounds |
| GB2088860B (en) * | 1980-12-09 | 1984-05-23 | Wyeth John & Brother Ltd | Process for preparing ring-fused pyridine derivatives |
| IE51857B1 (en) * | 1980-12-09 | 1987-04-15 | Wyeth John & Brother Ltd | Process for preparing pyridine derivatives |
| US4727149A (en) * | 1982-03-11 | 1988-02-23 | John Wyeth & Brother Limited | Preparation of nitriles of fused ring pyridine derivatives |
| US4539406A (en) * | 1982-06-25 | 1985-09-03 | John Wyeth & Brother Limited | Preparation of fused carbocyclic ring derivatives of pyridine |
| US4577022A (en) * | 1982-06-25 | 1986-03-18 | John Wyeth & Brother, Ltd. | Silyl compounds |
| GB2122992B (en) * | 1982-06-25 | 1986-12-03 | Wyeth John & Brother Ltd | Preparation of tetrahydroquinolines and related compounds |
| DE3233089A1 (en) * | 1982-09-07 | 1984-03-08 | Basf Ag, 6700 Ludwigshafen | CHINOLINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR CONTROLLING UNWANTED PLANT GROWTH |
| GB8301377D0 (en) * | 1983-01-19 | 1983-02-23 | Wyeth John & Brother Ltd | Quinoline derivatives |
| DE3645209C2 (en) * | 1986-08-27 | 1995-11-02 | Jagenberg Ag | Web winding machine winding sleeve inserter |
| IL112567A (en) * | 1994-02-10 | 2000-02-29 | Wyeth John & Brother Ltd | Substituted quinolines their preparation and pharmaceutical compositions containing them |
| IL112568A0 (en) * | 1994-02-10 | 1995-05-26 | Wyeth John & Brother Ltd | Substituted quinolines, their preparation and pharmaceutical compositions containing them |
| IL112566A (en) * | 1994-02-10 | 2000-10-31 | Wyeth John & Brother Ltd | Substituted quinolinones and pharmaceutical compositions containing them |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH46A (en) * | 1889-01-09 | Milovanovitsch Koka Kosta R | Rapid loading device for rear loading rifles | |
| DE2032738A1 (en) * | 1969-07-08 | 1971-01-21 | Takeda Chemical Industries, Ltd , Osaka (Japan) | Novel pyridinthioacetamiddenvate and process for their preparation |
-
1973
- 1973-02-15 GB GB742473*[A patent/GB1432378A/en not_active Expired
- 1973-09-17 CY CY996A patent/CY996A/en unknown
- 1973-10-10 AU AU61205/73A patent/AU474567B2/en not_active Expired
- 1973-10-16 AR AR250561A patent/AR203377A1/en active
- 1973-10-17 CH CH1469173A patent/CH602648A5/xx not_active IP Right Cessation
- 1973-10-17 CH CH75677A patent/CH592627A5/xx not_active IP Right Cessation
- 1973-10-18 NL NLAANVRAGE7314359,A patent/NL180213C/en active Search and Examination
- 1973-10-19 IN IN2330/CAL/73A patent/IN139235B/en unknown
- 1973-10-19 FR FR7337467A patent/FR2203634B1/fr not_active Expired
- 1973-10-19 PH PH15130A patent/PH12029A/en unknown
- 1973-10-19 DE DE19732352585 patent/DE2352585A1/en not_active Withdrawn
- 1973-10-19 IE IE1873/73A patent/IE38393B1/en unknown
- 1973-10-19 CA CA183,807A patent/CA1011741A/en not_active Expired
- 1973-10-19 FI FI3252/73A patent/FI52977C/fi active
-
1976
- 1976-03-03 PH PH18165A patent/PH12293A/en unknown
-
1977
- 1977-10-17 CH CH1001577A patent/CH601245A5/xx not_active IP Right Cessation
-
1979
- 1979-02-22 KE KE2922A patent/KE2922A/en unknown
- 1979-04-04 HK HK244/79A patent/HK24479A/en unknown
- 1979-12-31 MY MY1979173A patent/MY7900173A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1432378A (en) | 1976-04-14 |
| HK24479A (en) | 1979-04-12 |
| PH12293A (en) | 1978-12-29 |
| CA1011741A (en) | 1977-06-07 |
| NL7314359A (en) | 1974-04-23 |
| AU6120573A (en) | 1975-04-10 |
| NL180213C (en) | 1987-01-16 |
| IE38393B1 (en) | 1978-03-01 |
| PH12029A (en) | 1978-10-16 |
| CH601245A5 (en) | 1978-06-30 |
| IN139235B (en) | 1976-05-22 |
| FR2203634A1 (en) | 1974-05-17 |
| CH602648A5 (en) | 1978-07-31 |
| CH592627A5 (en) | 1977-10-31 |
| FI52977B (en) | 1977-09-30 |
| CY996A (en) | 1979-08-02 |
| FI52977C (en) | 1978-01-10 |
| KE2922A (en) | 1979-03-09 |
| DE2352585A1 (en) | 1974-05-09 |
| MY7900173A (en) | 1979-12-31 |
| FR2203634B1 (en) | 1977-09-09 |
| AU474567B2 (en) | 1976-07-29 |
| AR203377A1 (en) | 1975-09-08 |
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