19404-18-3

Usage

Chemical Properties

White to light yellow solid

InChI:InChI=1/C9H7ClS/c1-6-5-11-9-3-2-7(10)4-8(6)9/h2-5H,1H3

Upstream product

• 25784-83-2 (p-chlorophenylthio)acetone 
• 78-95-5 chloroacetone 
• 106-54-7 p-Chlorothiophenol 
• 71-43-2 benzene 

Downstream Products

• 98035-93-9 N-[(E)-3-tert-Butyl-5-(5-chloro-3-methyl-benzo[b]thiophen-2-yl)-pent-4-enyl]-2,2,2-trifluoro-acetamide 
• 1198-51-2 3-(bromomethyl)-5-chloro-1-benzothiophene 
• 51828-63-8 5-chloro-3-methyl-2-phenylbenzothiophen 
• 50451-78-0 5-chloro-3-methylbenzo[b]thiophene-2-carboxaldehyde 
• 212078-62-1 3-chloro-1-(5-chloro-3-methylbenzo[b]thiophen-2-yl)propan-1-one 
• 463976-34-3 6-(5-chloro-3-methylbenzothiophene-2-sulfonyl)-3-methoxypyridazine 
• 406235-96-9 methyl 4-(3-methyl-1-benzothien-5-yl)benzoate 
• 16296-68-7 5-chloro-benzo[b]thiophene-3-carbaldehyde 
• 1428338-26-4 (E)-5-chloro-3-methyl-2-(2-nitrovinyl)benzo[b]thiophene 
• 1447946-00-0 5-chloro-2-(4-chlorophenyl)-3-methylbenzo[b]thiophene 
• 1447946-04-4 5-chloro-3-methyl-2-naphthalen-2-yl-benzo[b]thiophene 
• 1447946-02-2 5-chloro-3-methyl-2-(3-nitrophenyl)-benzo[b]thiophene 
• 1447945-99-4 1-[4-(5-chloro-3-methylbenzo[b]thiophen-2-yl)-phenyl]-propan-1-one 
• 1447946-03-3 5-chloro-3-methyl-2-m-tolyl-benzo[b]thiophene 

Relevant academic research and scientific papers

TARGETED RADIOPHARMACEUTICALS FOR THE DIAGNOSIS AND TREATMENT OF PROSTATE CANCER

A compound of general formula (I): wherein: n is 1, 2 or 3; R1, R2, R3 and R4, independently represent OH or Q; and 20 Q represents a tissue-targeting moeity selected from the group consisting of or a stereoisomer, a hydrate, a solvate, or a salt thereof, or a mixture of same, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said 25 compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases, in particular of soft tissue diseases, as a sole agent or in combination with other active ingredients.

Heterocyclic compounds

The present invention relates to a novel heterocyclic compound or to pharmaceutically acceptable salts and solvates thereof. The pharmaceutical composition or cosmetic composition comprising, as active ingredients, the compound or pharmaceutically acceptable salts and solvates thereof may be effectively used in the treatment or prevention of skin diseases.

Preparation and pharmacological evaluation of a novel series of 2-(phenylthio)benzo[b]thiophenes as selective MT2 receptor ligands

A series of N-(2-(5-fluoro-2-(4-fluorophenylthio)benzo[b]thiophen-3-yl) ethyl)acylamides was synthesized and evaluated for binding affinity and intrinsic activity at melatonin receptors. The affinity of each compound for the melatonin receptors was determined by binding studies on cloned human MT 1 and MT2 receptors expressed in CHO cells. Agonist and antagonist potency was measured on the [35S]GTPγS binding assay for the most interesting compounds. The new derivatives 8-14 showed modest to high selectivity (between 4 and 220) for MT2 receptors. The most selective compound, N-(2-(5-fluoro-2-(4-fluorophenylthio)benzo[b]thiophen-3-yl) ethyl)but-3-enamide (14), an MT2 ligand with affinity for the MT 2 receptor similar to that of melatonin and a 220-fold preference over MT1 receptors, acts as a partial agonist. In addition, N-(2-(5-fluoro-2-(4-fluorophenylthio)benzo[b]thiophen-3-yl)ethyl)propionamide (9), a nanomolar MT2 ligand with a good selectivity ratio (MT 1/MT2 = 51) shows antagonist activity on both melatonin receptors.

C17,20-lyase inhibitors I. Structure-based de novo design and SAR study of C17,20-lyase inhibitors.

Novel nonsteroidal C(17,20)-lyase inhibitors were synthesized using de novo design based on its substrate, 17 alpha-hydroxypregnenolone, and several compounds exhibited potent C(17,20)-lyase inhibition. However, in vivo activities were found to be short-lasting, and in order to improve the duration of action, a series of benzothiophene derivatives were evaluated. As a result, compounds 9h, (S)-9i, and 9k with nanomolar enzyme inhibition (IC(50)=4-9 nM) and 9e (IC(50)=27 nM) were identified to have powerful in vivo efficacy with extended duration of action. The key structural determinants for the in vivo efficacy were demonstrated to be the 5-fluoro group on the benzothiophene ring and the 4-imidazolyl moiety. Superimposition of 9k and 17 alpha-hydroxypregnenolone demonstrated their structural similarity and enabled rationalization of the pharmacological results. In addition, selected compounds were also identified to be potent inhibitors of human enzyme with IC(50) values of 20-30 nM.

Use of alpha-1C specific compounds to treat benign prostatic hyperplasia

PCT No. PCT/US93/10950 Sec. 371 Date Apr. 1, 1997 Sec. 102(e) Date Apr. 1, 1997 PCT Filed Nov. 12, 1993 PCT Pub. No. WO94/10989 PCT Pub. Date May 26, 1994A method of treating benign prostatic hyperplasia in a subject which comprises administering to the subject a therapeutically effective amount of a compound which binds to a human alpha 1C adrenergic receptor with a binding affinity greater than ten-fold higher than the binding affinity with which the compound binds to a human alpha 1A adrenergic receptor, a human alpha 1B adrenergic receptor, and a human histamine H1 receptor, and, binds to a human alpha 2 adrenergic receptor with a binding affinity which is greater than ten-fold lower than the binding affinity with which the compound binds to such alpha 1C adrenergic receptor. Compounds meeting these criteria are provided.

DNA ENDODING HUMAN ALPHA 1 ADRENERGIC RECEPTORS

This invention provides an isolated nucleic acid, vectors, transformed mammalian cells and non-human transgenic animals that encode and express normal or mutant alpha 1a, alpha 1b and alpha 1c adrenergic receptor genes. This invention also provides a protein, and an antibody directed to the protein and pharmaceutical compounds related to alpha 1a, alpha 1b and alpha 1c adrenergic receptors. This invention provides nucleic acid probes, and antisense oligonucleotides complementary to alpha 1a, alpha 1b and alpha 1c adrenergic receptor genes. This invention further provides methods for determining ligand binding, detecting expression, drug screening, and treatments for alleviating abnormalities associated with human alpha 1a, alpha 1b and alpha 1c adrenergic receptors.

ALPHA1C SPECIFIC COMPOUNDS TO TREAT BENIGN PROSTATIC HYPERPLASIA

This invention provides a method of treating benign prostatic hyperplasia in a subject which comprises administering to the subject a therapeutically effective amount of an α 1C antagonist which (a) binds to a human α 1C adrenergic receptor with a binding affinity greater than 100-fold higher than the binding affinity with which the α 1C antagonist binds to a human α 1A adrenergic receptor, a human α 1B adrenergic receptor, and a human histamine H 1 receptor; and (b) binds to a human α 2 adrenergic receptor with a binding affinity which is greater than 100-fold lower than the binding affinity with which the α 1C antagonist binds to such α 1C adrenergic receptor.The invention further provides a method of inhibiting contraction of a prostate tissue which comprises contacting the prostate tissue with an effective contraction-inhibiting amount of an α 1C antagonist which (a) binds to a human α 1C adrenergic receptor with a binding affinity greater than 100-fold higher than the binding affinity with which the α 1C antagonist binds to a human α 1A adrenergic receptor, a human α 1B adrenergic receptor, and a human histamine H 1 receptor; and (b) binds to a human α 2 adrenergic receptor with a binding affinity which is greater than 100-fold lower than the binding affinity with which the α 1C antagonist binds to such α 1C adrenergic receptor.

Aromatic amine derivatives

This invention relates to novel aromatic amine compounds having the structure: STR1 where each W, Z1 and Z2 is independently H, C1 -C6 alkyl, C1 -C6 alkoxy, OH, F, Cl, Br, I, NO2, CN, SO2 NHR3, NR42, CONR32, COR5 ; where each R1 and R2 is independently H, C1 -C6 straight or branched chain alkyl or phenyl; where each X and Y is independently CH2, NR4, S, S=O, SO2 ; where n is 0, 1 or 2; where each p and q is independently 1 or 2; where R3 is H, C1 -C6 straight or branched chain alkyl or phenyl; where R4 is H, C1 -C6 straight or branched chain alkyl or COR3 ; and where R5 is H, C1 -C6 straight or branched chain alkyl or phenyl, C1 -C6 straight or branched chain alkoxy or OH. In addition the invention includes using such compounds for the treatment of benign prostatic hyperplasia, lowering intraocular pressure and inhibiting cholesterol synthesis.

USE OF ALPHA-1C SPECIFIC COMPOUNDS TO TREAT BENIGN PROSTATIC HYPERPLASIA

The subject invention provides a method of treating benign prostatic hyperplasia in a subject which comprises administering to the subject a therapeutically effective amount of a compound which binds to a human . alpha. 1C adrenergic receptor with a binding affinity greater than ten-fold higher than the binding affinity with which the compound binds to a human α 1A adrenergic receptor, a human α 1B adrenergic receptor, a human histamine H 1 receptor and α 2 adrenergic receptor. The subject invention also provides a method of inhibiting contraction of prostate tissue which comprises contacting the prostate tissue with an effective contraction-inhibiting amount of such compound.

Use of α1C specific compounds to treat benign prostatic hyperlasia

A method of treating benign prostatic hyperplasia in a subject which comprises administering to the subject a therapeutically effective amount of a compound which binds to a human α1C adrenergic receptor with a binding affinity greater than ten-fold higher than the binding affinity with which the compound binds to a human α1A adrenergic receptor, a human α1B adrenergic receptor, and a human histamine H1 receptor, and, binds to a human α2 adrenergic receptor with a binding affinity which is greater than ten-fold lower than the binding affinity with which the compound binds to such α1C adrenergic receptor. Compounds meeting these criteria are provided.