GB1370028A - Substituted indenyl acetic acid derivatives - Google Patents
Substituted indenyl acetic acid derivativesInfo
- Publication number
- GB1370028A GB1370028A GB219672A GB219672A GB1370028A GB 1370028 A GB1370028 A GB 1370028A GB 219672 A GB219672 A GB 219672A GB 219672 A GB219672 A GB 219672A GB 1370028 A GB1370028 A GB 1370028A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- hydrogen
- prepared
- reaction
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- PTUSXMWNCXRKAX-UHFFFAOYSA-N 2-(1h-inden-1-yl)acetic acid Chemical class C1=CC=C2C(CC(=O)O)C=CC2=C1 PTUSXMWNCXRKAX-UHFFFAOYSA-N 0.000 title abstract 2
- -1 N-morpholino, piperidino, pyrrolidino, piperazino Chemical group 0.000 abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract 7
- 239000001257 hydrogen Substances 0.000 abstract 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 5
- 238000006243 chemical reaction Methods 0.000 abstract 5
- 150000002431 hydrogen Chemical class 0.000 abstract 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 5
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- SOOARYARZPXNAL-UHFFFAOYSA-N 2-(Methylthio)phenol Chemical compound CSC1=CC=CC=C1O SOOARYARZPXNAL-UHFFFAOYSA-N 0.000 abstract 2
- PDODBKYPSUYQGT-UHFFFAOYSA-N acetic acid;1h-indene Chemical class CC(O)=O.C1=CC=C2CC=CC2=C1 PDODBKYPSUYQGT-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 2
- 125000001188 haloalkyl group Chemical group 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 230000001590 oxidative effect Effects 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 abstract 1
- KMGHCDZLSCNMDC-UHFFFAOYSA-N 1,2-bis(methylsulfanyl)benzene Chemical compound CSC1=CC=CC=C1SC KMGHCDZLSCNMDC-UHFFFAOYSA-N 0.000 abstract 1
- IHLDFHCSSCVPQW-UHFFFAOYSA-N 1-chloro-2-methylsulfanylbenzene Chemical compound CSC1=CC=CC=C1Cl IHLDFHCSSCVPQW-UHFFFAOYSA-N 0.000 abstract 1
- CTUPBAXICGISQP-UHFFFAOYSA-N 2-methylthiobenzaldehyde Chemical compound CC1=CC=CC=C1C=S CTUPBAXICGISQP-UHFFFAOYSA-N 0.000 abstract 1
- SKPMCQCNBCKGNA-UHFFFAOYSA-N 3,4-dimethylthiobenzaldehyde Chemical compound CC1=CC=C(C=S)C=C1C SKPMCQCNBCKGNA-UHFFFAOYSA-N 0.000 abstract 1
- AKQUMDSKAOMFAD-UHFFFAOYSA-N 3-(4-acetylphenyl)-2-methylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=C(C(C)=O)C=C1 AKQUMDSKAOMFAD-UHFFFAOYSA-N 0.000 abstract 1
- KVFUMBHERGZEGG-UHFFFAOYSA-N 3-hydroxy-4-methylthiobenzaldehyde Chemical compound CC1=CC=C(C=S)C=C1O KVFUMBHERGZEGG-UHFFFAOYSA-N 0.000 abstract 1
- KTFKRVMXIVSARW-UHFFFAOYSA-N 4-acetylbenzaldehyde Chemical compound CC(=O)C1=CC=C(C=O)C=C1 KTFKRVMXIVSARW-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- 238000006680 Reformatsky reaction Methods 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 230000017858 demethylation Effects 0.000 abstract 1
- 238000010520 demethylation reaction Methods 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- GRTGGSXWHGKRSB-UHFFFAOYSA-N dichloromethyl methyl ether Chemical compound COC(Cl)Cl GRTGGSXWHGKRSB-UHFFFAOYSA-N 0.000 abstract 1
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 abstract 1
- 125000005191 hydroxyalkylamino group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 abstract 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 1
- 229920000137 polyphosphoric acid Polymers 0.000 abstract 1
- 235000019260 propionic acid Nutrition 0.000 abstract 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 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 125000004001 thioalkyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10862771A | 1971-01-21 | 1971-01-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1370028A true GB1370028A (en) | 1974-10-09 |
Family
ID=22323233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB219672A Expired GB1370028A (en) | 1971-01-21 | 1972-01-17 | Substituted indenyl acetic acid derivatives |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5654313B1 (enrdf_load_stackoverflow) |
| AU (1) | AU470567B2 (enrdf_load_stackoverflow) |
| CA (1) | CA983951A (enrdf_load_stackoverflow) |
| CH (1) | CH574405A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2202715A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2122589B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1370028A (enrdf_load_stackoverflow) |
| NL (1) | NL7200058A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2274725A1 (es) * | 2005-11-08 | 2007-05-16 | Laboratorios Del Dr. Esteve, S.A. | Indeno derivados, su preparacion y su uso como medicamentos. |
| WO2016100546A1 (en) | 2014-12-16 | 2016-06-23 | Adt Pharmaceuticals, Inc. | Method of treating or preventing ras-mediated diseases |
| WO2016100542A1 (en) | 2014-12-16 | 2016-06-23 | Adt Pharmaceuticals, Inc. | Indenyl compounds, pharmaceutical compositions, and medical uses thereof |
| WO2019210223A1 (en) | 2018-04-26 | 2019-10-31 | Adt Pharmaceuticals, Llc | Anticancer indenes, indanes, azaindenes, azaindanes, pharmaceutical compositions and uses |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE426818B (sv) * | 1973-12-20 | 1983-02-14 | Merck & Co Inc | Forfarande for framstellning av 5-fluor-2-metyl-1-(p-metylsulfinylbesyliden)-inden-3-ettiksyra eller dess syraadditionssalt |
| GR71725B (enrdf_load_stackoverflow) * | 1977-11-10 | 1983-06-22 | Hoffmann La Roche | |
| US6214876B1 (en) * | 1994-07-21 | 2001-04-10 | Eli Lilly And Company | Indene-1-acetamide sPLA2 inhibitors |
-
1972
- 1972-01-04 NL NL7200058A patent/NL7200058A/xx not_active Application Discontinuation
- 1972-01-11 AU AU37792/72A patent/AU470567B2/en not_active Expired
- 1972-01-11 CA CA132,200A patent/CA983951A/en not_active Expired
- 1972-01-11 CH CH37072A patent/CH574405A5/xx not_active IP Right Cessation
- 1972-01-17 GB GB219672A patent/GB1370028A/en not_active Expired
- 1972-01-20 DE DE19722202715 patent/DE2202715A1/de active Pending
- 1972-01-21 FR FR7202071A patent/FR2122589B1/fr not_active Expired
- 1972-01-21 JP JP769772A patent/JPS5654313B1/ja active Pending
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2274725A1 (es) * | 2005-11-08 | 2007-05-16 | Laboratorios Del Dr. Esteve, S.A. | Indeno derivados, su preparacion y su uso como medicamentos. |
| ES2274725B1 (es) * | 2005-11-08 | 2008-04-01 | Laboratorios Del Dr. Esteve, S.A. | Indeno derivados, su preparacion y su uso como medicamentos. |
| EP3666268A1 (en) | 2014-12-16 | 2020-06-17 | ADT Pharmaceuticals, LLC | Method of treating or preventing ras-mediated diseases |
| US11130744B2 (en) | 2014-12-16 | 2021-09-28 | Adt Pharmaceuticals, Llc | Indenyl compounds, pharmaceutical compositions, and medical uses thereof |
| US9862698B2 (en) | 2014-12-16 | 2018-01-09 | Adt Pharmaceuticals, Inc. | Indenyl compounds, pharmaceutical compositions, and medical uses thereof |
| US9931315B2 (en) | 2014-12-16 | 2018-04-03 | Adt Pharmaceuticals, Inc. | Method of selectively inhibiting Ras-mediated tumor growth in humans |
| EP4053105A1 (en) | 2014-12-16 | 2022-09-07 | ADT Pharmaceuticals, LLC | Indenyl compounds, pharmaceutical compositions, and medical uses thereof |
| US10526307B2 (en) | 2014-12-16 | 2020-01-07 | Adt Pharmaceuticals, Llc | Indenyl compounds, pharmaceutical compositions, and medical uses thereof |
| WO2016100546A1 (en) | 2014-12-16 | 2016-06-23 | Adt Pharmaceuticals, Inc. | Method of treating or preventing ras-mediated diseases |
| US10975054B2 (en) | 2014-12-16 | 2021-04-13 | Adt Pharmaceuticals, Llc | Indenyl compounds, pharmaceutical compositions, and medical uses thereof |
| US10981886B2 (en) | 2014-12-16 | 2021-04-20 | Adt Pharmaceuticals, Llc | Indenyl compounds, pharmaceutical compositions, and medical uses thereof |
| US11104658B2 (en) | 2014-12-16 | 2021-08-31 | Adt Pharmaceuticals, Llc | Method of treating or preventing Ras-mediated diseases |
| WO2016100542A1 (en) | 2014-12-16 | 2016-06-23 | Adt Pharmaceuticals, Inc. | Indenyl compounds, pharmaceutical compositions, and medical uses thereof |
| US11407727B2 (en) | 2014-12-16 | 2022-08-09 | Adt Pharmaceuticals, Llc | Indenyl compounds, pharmaceutical compositions, and medical uses thereof |
| US11198679B2 (en) | 2014-12-16 | 2021-12-14 | Adt Pharmaceuticals, Llc | Method of treating or preventing Ras-mediated diseases |
| US11186596B2 (en) | 2018-04-26 | 2021-11-30 | Adt Pharmaceuticals, Llc | Anticancer indenes, indanes, azaindenes, azaindanes, pharmaceutical compositions and uses |
| WO2019210223A1 (en) | 2018-04-26 | 2019-10-31 | Adt Pharmaceuticals, Llc | Anticancer indenes, indanes, azaindenes, azaindanes, pharmaceutical compositions and uses |
| US11680073B2 (en) | 2018-04-26 | 2023-06-20 | Adt Pharmaceuticals, Llc | Anticancer indenes, indanes, azaindenes, azaindanes, pharmaceutical compositions and uses |
Also Published As
| Publication number | Publication date |
|---|---|
| AU470567B2 (en) | 1976-03-18 |
| DE2202715A1 (de) | 1972-07-27 |
| FR2122589A1 (enrdf_load_stackoverflow) | 1972-09-01 |
| NL7200058A (enrdf_load_stackoverflow) | 1972-07-25 |
| AU3779272A (en) | 1973-07-12 |
| CH574405A5 (enrdf_load_stackoverflow) | 1976-04-15 |
| CA983951A (en) | 1976-02-17 |
| JPS5654313B1 (enrdf_load_stackoverflow) | 1981-12-24 |
| FR2122589B1 (enrdf_load_stackoverflow) | 1975-02-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |