IL41130A - Fused indole and indene derivatives and their preparation - Google Patents
Fused indole and indene derivatives and their preparationInfo
- Publication number
- IL41130A IL41130A IL41130A IL4113072A IL41130A IL 41130 A IL41130 A IL 41130A IL 41130 A IL41130 A IL 41130A IL 4113072 A IL4113072 A IL 4113072A IL 41130 A IL41130 A IL 41130A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- formula
- treating
- hydrogen
- group
- Prior art date
Links
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title 2
- 125000003454 indenyl group Chemical class C1(C=CC2=CC=CC=C12)* 0.000 title 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 54
- 239000001257 hydrogen Substances 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 15
- 239000002253 acid Substances 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 238000000034 method Methods 0.000 claims 8
- 230000009466 transformation Effects 0.000 claims 8
- 150000001412 amines Chemical class 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 230000003301 hydrolyzing effect Effects 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 3
- 239000003377 acid catalyst Substances 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 150000003138 primary alcohols Chemical class 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims 1
- 241000282320 Panthera leo Species 0.000 claims 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims 1
- 229940125782 compound 2 Drugs 0.000 claims 1
- 229940126214 compound 3 Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- -1 piperazino Chemical group 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 238000010561 standard procedure Methods 0.000 claims 1
- 238000000844 transformation Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/02—Thiols having mercapto groups bound to acyclic carbon atoms
- C07C321/10—Thiols having mercapto groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (1)
1. We process for preparing a compound of formula in which R is lower R R R and R are the same or different and are selected from the group consisting of hydrogen and lower and are the same or different and are selected from the group consisting of hydrogen and lower or R 6 and R 7 together with the nitrogen atom to which they are joined saturated form ic amine radical selected from the group sisting of alky and is an alkylene selected from the group sisting of and V5 wherein R R 15 and are hydrogen or lower X is oxy or thio and A is a divalent radical selected from the group consisting of in which R is hydrogen or lower alkyl R is alkyl and R is lower alkyl lower lower alkanoyloxy or which comprises treating a compound formu la 4 5 2 3 R CR R Y in which B is a monovalent radical selected from the group consisting of which and are as defined and 5 R are as defined herein and Y is or with a compound of formula in which is as defined herein and Z is selected from the group consisting of which and R7 are as and C00R19 in which is hydrogen or lower alkyl and is an alkylene selected from the group consisting of and wherein R10 and are hydrogen or lower CONRV and in which Alk1 R6 and R7 are as 20 I 20 20 and Alk in which is hydrogen or lower alkyl and is as defined 2 2 Alk in which Alk is an alkylene selected from the group consisting of and wherein R R R R R R and R are as defined herein and L is in which and R6 are as defined herein and is hydrogen or lower a Iky I containing from one to five carboo and in which Alk is as defined in the presence of acid catalyst to obtain the corresponding 2 4 5 compound of formula V In which R R R R R X and Z are as defined fol when said of formu la is different from said compound of formula by transformation of said compound of formula into a compound of by the application of standard methods known to be effective for said transformations for other A process as claimed in Claim characterized by 2 3 4 5 treating a compound of the formula in R R R R and Y are as defined therein with a compound of the formula 1 in which R is as defined therein and Z is AlkrNR R as defined in the presence of an acid to obtain 2 3 the corresponding compound of formula IV which R R R R5 and X are as defined therein and Z is as defined A process as claimed in Claim characterized 2 3 4 by treating a compound of formula I in which R R R 5 R and Y are as defined therein with a compound of formula I in which R is as defined therein and Z is COOR or 1 I 1 wherein Alk is as defined therein and R is lower in the present of an acid to obtain the corresponding compound of formula IV in which 2 3 4 5 R R R R R and X are as defined therein and Z is COOR19 or wherein is as defined 19 therein and R is lower followed by of said last named compound to the corresponding compound of formula by treating said last named compound with a hydrolyzing agent to obtain the corresponding acid of formula in which Z is COOH or as defined treating the corresponding acid of formula JV with a lower alkyl ch Ioroformate to obtain the corresponding mixed treating the mixed anhydride with an amine of formula HNR6R7 in which and R7 are as defined therein to obtain the corresponding amide of formula in which Z is or and treating the last named compound with a reducing A process as claimed in Claim characterized 2 3 4 by treating a compound of formula I in which B R R R 5 R and Y are as defined therein with a compound of formula in which is as defined therein and Z is C0NR6R7 or wherein and are as defined in the presence of an acid cata to obtain the i ng 1 2 3 4 5 compound of formula JV in which R R R R R and X are as defined therein and Z is or k as defined by transformation of said last named compound to the compound of formula by treating said last named compound with a reducing A process as claimed in Claim I characterized 2 3 by treating a compound of formula in which R R 4 5 R R and Y are as defined therein with a compound of formula in which is as defined therein and Z is CH20C0R20 or A I wherein R20 and are as defined therein in the presence of an acid catalyst to obtain the corresponding compound of formula in which 2 3 4 5 R R R R R and X are as defined therein and Z is CH20C0R20 or A I as defined followed by transformation of last named compound to the corresponding compound of formula by treating said last named compound with a hydrolyzing agent to obtain the corresponding primary alcohol of formula in which Z is or treating the primary alcohol with a ha logenating mesylating or tosylating agent to obtain the corresponding mesylate or and treating said last named 67 6 7 compound with an amine of formula HNR R in which R and R are as defined A process as claimed in Claim I characterized 2 3 4 by treating a compound of formula in which B R R R 5 R and Y are as defined therein with a compound of formula I 2 in which R is as defined therein and Z is Alk wherein 2 Alk and L are as defined in the presence of an acid to obtain the compound 2 3 4 5 of formula in which R R R R R and X are 2 as defined therein and Z is Alk as defined followed by transformation of said last named compound to the corresponding compound of formula by treating said last named compound with an amine of formula 67 7 HNR R in which R and R are as defined A process as claimed in Claim characterized by treating a compound of formula 2 3 4 5 in which R R R R and Y are as defined therein with a compound of formula in which is as defined 6 therein and Z is COR R and R are as defined in the presence of an acid to obtain the corresponding compound of formula which 1 3 4 5 R R R R R and X are as defined therein and Z 6 1 is COR as defined followed by transformation of said last named compound to the corresponding compound of formula by treating said last named compound with a reducing A process as claimed in Claim characterized 2 3 by treating a compound of formula in which B R R 4 5 R R and Y are as defined therein with a compound of formula in which is as defined therein and Z is wherein Alk as defined in the presence of an acid to obtain the corresponding compound 3 4 5 of formula JV in which R R R R R and X are as defined therein and Z is as defined followed by transformation of said named compound to the corresponding compound of formula by said last named compound with a reducing A process as claimed in Claim characterized by treating a compound of formula in which B wherein is hydrogen and is as defined therein and 2 4 R R R R and Y are as defined therein with a compound of formula I in which is as therein and Z is C00R19 or wherein is as defined therein 19 and R is lower alky I in the present of an acid to obtain the corresponding compound of formula in which A is wherein is hydrogen and is as defined therein and and X are as defined therein and Z is 19 I 19 I COOR or Alk wherein Alk is as defined therein and 19 R is lower followed by transformation of said last named compound to the corresponding compound of formula in which A is wherein is lower alkyl and is as defined therein by treating said last named compound of formula with a hydrolyzing agent to obtain the corresponding acid of formula JV in which Z is COOH or as defined the corresponding acid of formula IV with lower alkyl to obtain the corresponding lated acid of formula treating the acid with a lower a Iky ch loroformate to obtain the mixed treating the mixed anhydride with ah amine of formula in which R6 and R7 are as defined therein to obtain the corresponding amide in which Z is C0NR6R7 or and treating the last named compound with a reducing A compound of in which is lower alky and R5 are the same or different and are selected from the group of hydrogen and lower alky and are the same or different and are selected from the group consisting of hydrogen and lower or R6 and together with the nitrogen atom to which they are joined form ar heterocyc c amine radical selected from the group sisting of piperazino alky and Alk is alk lene selected from group sisting of and wherein and are hydrogen or lower X is oxy or thio and A is a divalent radical selected from the group g of in which R is hydrogen or lower alky lower alky and R hydrogen lower lower lowe alkanoyloxy or as claimed in Claim as claimed laim as claimed in Claim as claimed in Claim as claimed in Claim as claimed in Claim as claimed in Claim as claimed in Claim as claimed in Claim as claimed in Claim as claimed in Claim as claimed Claim i as claimed in Claim A composi which comprises f a 2 3 4 5 in which R is lower R R and R are the same or different and are selected from the group consisting of and lower alky and R7 are the same or different and are selected from the group consisting of hydrogen and lower or 6 7 R and R together with the nitrogen atom to are joined form a heterocyclic amine radical selected from the group sisting of lower and an alk selected from group sisting of and wherein R and R are hydrogen or lower X is oxy or thio and A is a divalent radical selected from the group consisting of in which R is hydrogen or lower R 18 and R is lower lower lower alkano and a pharmaceutically acceptable carrier for the insufficientOCRQuality
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00217627A US3852285A (en) | 1972-01-13 | 1972-01-13 | Pyrano- and thiopyranoindole derivatives |
| US00226287A US3833575A (en) | 1972-02-14 | 1972-02-14 | Oxazinoindole-and thiazinoindole derivatives |
| US29712972A | 1972-10-12 | 1972-10-12 | |
| US297130A US3904617A (en) | 1972-10-12 | 1972-10-12 | Process for preparing new heterocyclic derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL41130A0 IL41130A0 (en) | 1973-02-28 |
| IL41130A true IL41130A (en) | 1976-05-31 |
Family
ID=27499082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL41130A IL41130A (en) | 1972-01-13 | 1972-12-20 | Fused indole and indene derivatives and their preparation |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE793978A (en) |
| CH (3) | CH606031A5 (en) |
| DK (1) | DK141201B (en) |
| IL (1) | IL41130A (en) |
| NL (1) | NL7300518A (en) |
| SE (1) | SE392274B (en) |
| SU (1) | SU728716A3 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1683521A1 (en) * | 2005-01-21 | 2006-07-26 | Centre National De La Recherche Scientifique (Cnrs) | Peptide deformylase inhibitors, their use, and pharmaceutical compositions containing the same |
-
0
- BE BE793978D patent/BE793978A/en not_active IP Right Cessation
-
1972
- 1972-12-20 IL IL41130A patent/IL41130A/en unknown
-
1973
- 1973-01-12 CH CH1530777A patent/CH606031A5/xx not_active IP Right Cessation
- 1973-01-12 DK DK20973AA patent/DK141201B/en unknown
- 1973-01-12 SU SU731873352A patent/SU728716A3/en active
- 1973-01-12 SE SE7300471A patent/SE392274B/en unknown
- 1973-01-12 CH CH48773A patent/CH605959A5/en not_active IP Right Cessation
- 1973-01-12 CH CH1530677A patent/CH606030A5/xx not_active IP Right Cessation
- 1973-01-12 NL NL7300518A patent/NL7300518A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DK141201C (en) | 1980-07-28 |
| SU728716A3 (en) | 1980-04-15 |
| DK141201B (en) | 1980-02-04 |
| CH606030A5 (en) | 1978-10-13 |
| CH606031A5 (en) | 1978-10-13 |
| CH605959A5 (en) | 1978-10-13 |
| IL41130A0 (en) | 1973-02-28 |
| SE392274B (en) | 1977-03-21 |
| NL7300518A (en) | 1973-07-17 |
| BE793978A (en) | 1973-07-12 |
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