CA3092144A1 - Diphenyl substituted thiophene-2-amide derivatives and pharmaceutical compositions thereof useful as antimicrobial - Google Patents

Diphenyl substituted thiophene-2-amide derivatives and pharmaceutical compositions thereof useful as antimicrobial Download PDF

Info

Publication number
CA3092144A1
CA3092144A1 CA3092144A CA3092144A CA3092144A1 CA 3092144 A1 CA3092144 A1 CA 3092144A1 CA 3092144 A CA3092144 A CA 3092144A CA 3092144 A CA3092144 A CA 3092144A CA 3092144 A1 CA3092144 A1 CA 3092144A1
Authority
CA
Canada
Prior art keywords
compound
antimicrobial
microbial infection
treatment
compounds
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.)
Pending
Application number
CA3092144A
Other languages
English (en)
French (fr)
Inventor
Fan Wu
Erhu Lu
Shengguo Sun
Christopher J. Barden
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Denovamed Inc
Original Assignee
Denovamed Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Denovamed Inc filed Critical Denovamed Inc
Publication of CA3092144A1 publication Critical patent/CA3092144A1/en
Pending legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/34—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/36—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/429—Thiazoles condensed with heterocyclic ring systems
    • A61K31/43—Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula, e.g. penicillins, penems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Immunology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA3092144A 2018-03-05 2019-03-01 Diphenyl substituted thiophene-2-amide derivatives and pharmaceutical compositions thereof useful as antimicrobial Pending CA3092144A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201862638832P 2018-03-05 2018-03-05
US62/638,832 2018-03-05
US201862727809P 2018-09-06 2018-09-06
US62/727,809 2018-09-06
PCT/CA2019/050242 WO2019169479A1 (en) 2018-03-05 2019-03-01 Diphenyl substituted thiophene-2-amide derivatives and pharmaceutical compositions thereof useful as antimicrobial

Publications (1)

Publication Number Publication Date
CA3092144A1 true CA3092144A1 (en) 2019-09-12

Family

ID=67846467

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3092144A Pending CA3092144A1 (en) 2018-03-05 2019-03-01 Diphenyl substituted thiophene-2-amide derivatives and pharmaceutical compositions thereof useful as antimicrobial

Country Status (7)

Country Link
US (1) US11306067B2 (https=)
EP (1) EP3762376B1 (https=)
JP (1) JP7309214B2 (https=)
CN (1) CN112166109B (https=)
CA (1) CA3092144A1 (https=)
ES (1) ES2942848T3 (https=)
WO (1) WO2019169479A1 (https=)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023193101A1 (en) * 2022-04-05 2023-10-12 Denovamed Inc. Antibacterial 4,5 diaryl-thiophen-2-yl hexafluoropropan-2-ols

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113855680B (zh) * 2021-09-02 2023-11-03 四川农业大学 肉桂醛联合头孢曲松钠的应用

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1011949A (en) 1964-10-27 1965-12-01 Vacu Blast Ltd Centrifugal wheel blasting machine
US3527864A (en) 1966-11-18 1970-09-08 Procter & Gamble Compositions for topical application to animal tissue and method of enhancing penetration thereof
US3472931A (en) 1969-01-17 1969-10-14 Foster Milburn Co Percutaneous absorption with lower alkyl amides
US3903256A (en) 1972-02-07 1975-09-02 Procter & Gamble Compositions for topical application of animal tissue and method of enhancing penetration thereof
US3896238A (en) 1972-04-05 1975-07-22 Procter & Gamble Dermatological compositions
US3952099A (en) 1973-03-13 1976-04-20 The Procter & Gamble Company Dermatological compositions
US4046886A (en) 1975-01-17 1977-09-06 The Procter & Gamble Company Dermatological compositions
US4405616A (en) 1975-06-19 1983-09-20 Nelson Research & Development Company Penetration enhancers for transdermal drug delivery of systemic agents
US4130643A (en) 1976-01-12 1978-12-19 The Procter & Gamble Company Dermatological compositions
US4335115A (en) 1976-11-01 1982-06-15 The Procter & Gamble Company Anti-acne composition
US4299826A (en) 1979-10-12 1981-11-10 The Procter & Gamble Company Anti-acne composition
JPS57134480A (en) * 1980-12-29 1982-08-19 Du Pont Antiinflammatory 4,5-diaryl-alpha- (polyhalomethyl)-2-thiophene methanols
US4379454A (en) 1981-02-17 1983-04-12 Alza Corporation Dosage for coadministering drug and percutaneous absorption enhancer
US4343798A (en) 1981-06-23 1982-08-10 The Procter & Gamble Company Topical antimicrobial anti-inflammatory compositions
US4863970A (en) 1986-11-14 1989-09-05 Theratech, Inc. Penetration enhancement with binary system of oleic acid, oleins, and oleyl alcohol with lower alcohols
US4746515A (en) 1987-02-26 1988-05-24 Alza Corporation Skin permeation enhancer compositions using glycerol monolaurate
US4788062A (en) 1987-02-26 1988-11-29 Alza Corporation Transdermal administration of progesterone, estradiol esters, and mixtures thereof
US4820720A (en) 1987-08-24 1989-04-11 Alza Corporation Transdermal drug composition with dual permeation enhancers
US4863738A (en) 1987-11-23 1989-09-05 Alza Corporation Skin permeation enhancer compositions using glycerol monooleate
US5378730A (en) 1988-06-09 1995-01-03 Alza Corporation Permeation enhancer comprising ethanol and monoglycerides
GB9012936D0 (en) 1990-06-11 1990-08-01 Fujisawa Pharmaceutical Co Thiophene derivatives,processes for preparation thereof and pharmaceutical composition comprising the same
US6835745B2 (en) 2002-01-15 2004-12-28 Wyeth Phenyl substituted thiophenes as estrogenic agents
FR2860792B1 (fr) 2003-10-10 2006-02-24 Sanofi Synthelabo Derives de thiophene-2-carboxamide, leur preparation et leur application en therapeutique
CN103619836A (zh) * 2011-03-03 2014-03-05 德诺瓦姆德有限公司 抗菌剂/抗菌佐剂化合物及其方法

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023193101A1 (en) * 2022-04-05 2023-10-12 Denovamed Inc. Antibacterial 4,5 diaryl-thiophen-2-yl hexafluoropropan-2-ols

Also Published As

Publication number Publication date
CN112166109B (zh) 2023-09-12
US11306067B2 (en) 2022-04-19
ES2942848T3 (es) 2023-06-07
EP3762376A1 (en) 2021-01-13
EP3762376B1 (en) 2023-03-01
JP2021516680A (ja) 2021-07-08
JP7309214B2 (ja) 2023-07-18
CN112166109A (zh) 2021-01-01
US20210017147A1 (en) 2021-01-21
WO2019169479A1 (en) 2019-09-12
EP3762376A4 (en) 2021-10-20

Similar Documents

Publication Publication Date Title
EP2651419B1 (en) A composition comprising an antibiotic and a dispersant
EP2681208B1 (en) Antimicrobial/adjuvant compounds
JP5410748B2 (ja) 抗菌剤およびカルベオール、チモール、オイゲノール、ボルネオールならびにカルバクロールから選択される活性成分を含んでなる医薬組成物
WO2013139861A1 (en) Methods and pharmaceutical compositions of the treatment of autistic syndrome disorders
EP2889034A2 (en) Compositions and methods of treatment comprising ceftaroline
US11306067B2 (en) Diphenyl substituted thiophene-2-amide derivatives and pharmaceutical compositions thereof useful as antimicrobial
EP1689405B1 (en) Thioridazine and derivatives thereof for reversing anti-microbial drug-resistance
EP4504714A1 (en) Antibacterial 4,5 diaryl-thiophen-2-yl hexafluoropropan-2-ols
JP2015105267A (ja) 併用抗メチシリン耐性黄色ブドウ球菌薬、及びβラクタム系抗生物質の抗菌活性増強剤
HK1185015B (en) A composition comprising an antibiotic and a dispersant
WO2016180919A1 (en) Enhanced antibiotic composition

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20231206

D15 Examination report completed

Free format text: ST27 STATUS EVENT CODE: A-2-2-D10-D15-D126 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: EXAMINER'S REPORT

Effective date: 20241223

P11 Amendment of application requested

Free format text: ST27 STATUS EVENT CODE: A-2-2-P10-P11-P100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: AMENDMENT RECEIVED - RESPONSE TO EXAMINER'S REQUISITION

Effective date: 20250204

MFA Maintenance fee for application paid

Free format text: FEE DESCRIPTION TEXT: MF (APPLICATION, 6TH ANNIV.) - SMALL

Year of fee payment: 6

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-2-2-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20250206

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-2-2-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT DETERMINED COMPLIANT

Effective date: 20250206

Free format text: ST27 STATUS EVENT CODE: A-2-2-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20250206

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: A-2-2-W10-W00-W111 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: CORRESPONDENT DETERMINED COMPLIANT

Effective date: 20250221

P11 Amendment of application requested

Free format text: ST27 STATUS EVENT CODE: A-2-2-P10-P11-P102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: AMENDMENT DETERMINED COMPLIANT

Effective date: 20250703

P13 Application amended

Free format text: ST27 STATUS EVENT CODE: A-2-2-P10-P13-X000 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: APPLICATION AMENDED

Effective date: 20250703

MFA Maintenance fee for application paid

Free format text: FEE DESCRIPTION TEXT: MF (APPLICATION, 7TH ANNIV.) - SMALL

Year of fee payment: 7

U00 Fee paid

Free format text: ST27 STATUS EVENT CODE: A-2-2-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED

Effective date: 20251218

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-2-2-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL

Effective date: 20251218

D00 Search and/or examination requested or commenced

Free format text: ST27 STATUS EVENT CODE: A-2-2-D10-D00-D149 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: EXAMINER'S INTERVIEW

Effective date: 20260105

P11 Amendment of application requested

Free format text: ST27 STATUS EVENT CODE: A-2-2-P10-P11-P101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: AMENDMENT RECEIVED - VOLUNTARY AMENDMENT

Effective date: 20260105

P11 Amendment of application requested

Free format text: ST27 STATUS EVENT CODE: A-2-2-P10-P11-P102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: AMENDMENT DETERMINED COMPLIANT

Effective date: 20260113

P13 Application amended

Free format text: ST27 STATUS EVENT CODE: A-2-2-P10-P13-X000 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: APPLICATION AMENDED

Effective date: 20260113

W00 Other event occurred

Free format text: ST27 STATUS EVENT CODE: A-2-2-W10-W00-W111 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: CORRESPONDENT DETERMINED COMPLIANT

Effective date: 20260113