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Also known as: 935283-04-8, Linzagolix [inn], Linzagolix [usan], Obe-2109, 7cdw97huex, Obe2109
Molecular Formula
C22H15F3N2O7S
Molecular Weight
508.4  g/mol
InChI Key
BMAAMIIYNNPHAB-UHFFFAOYSA-N
FDA UNII
7CDW97HUEX

Linzagolix
Linzagolix is an orally bioavailable gonadotropin-releasing hormone (GnRH or LHRH) receptor antagonist, with potential hormone production inhibitory activity. Upon oral administration of linzagolix, this agent competes with GnRH for receptor binding and inhibits GnRH receptor signaling in the anterior pituitary gland, thereby inhibiting the secretion and release of luteinizing hormone (LH) and follicle stimulating hormone (FSH). In males, the inhibition of LH secretion prevents the release of testosterone. As a result, this may relieve symptoms associated with hormonally dependent disease states such as hormone-dependent prostate cancer. In women, this prevents the production of estrogen by the ovaries and may relieve symptoms from sex-hormone dependent diseases, such as pain associated with endometriosis, heavy menstrual bleeding or uterine fibroids.
1 2D Structure

Linzagolix

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-[5-[(2,3-difluoro-6-methoxyphenyl)methoxy]-2-fluoro-4-methoxyphenyl]-2,4-dioxo-1H-thieno[3,4-d]pyrimidine-5-carboxylic acid
2.1.2 InChI
InChI=1S/C22H15F3N2O7S/c1-32-14-4-3-10(23)18(25)9(14)7-34-16-6-13(11(24)5-15(16)33-2)27-20(28)17-12(26-22(27)31)8-35-19(17)21(29)30/h3-6,8H,7H2,1-2H3,(H,26,31)(H,29,30)
2.1.3 InChI Key
BMAAMIIYNNPHAB-UHFFFAOYSA-N
2.1.4 Canonical SMILES
COC1=C(C(=C(C=C1)F)F)COC2=C(C=C(C(=C2)N3C(=O)C4=C(SC=C4NC3=O)C(=O)O)F)OC
2.2 Other Identifiers
2.2.1 UNII
7CDW97HUEX
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3-(5-((2,3-difluoro-6-methoxyphenyl)methoxy)-2-fluoro-4-methoxyphenyl)-2,4-dioxo-1h-thieno(3,4-d)pyrimidine-5-carboxylic Acid

2. Klh-2109

3. Klh2109

4. Obe-2109

5. Obe2109

2.3.2 Depositor-Supplied Synonyms

1. 935283-04-8

2. Linzagolix [inn]

3. Linzagolix [usan]

4. Obe-2109

5. 7cdw97huex

6. Obe2109

7. Klh-2109

8. Klh-2109; Obe-2109

9. 3-{5-[(2,3-difluoro-6-methoxyphenyl)methoxy]-2-fluoro-4-methoxyphenyl}-2,4-dioxo-1,2,3,4-tetrahydrothieno[3,4-d]pyrimidine-5-carboxylic Acid

10. Thieno(3,4-d)pyrimidine-5-carboxylic Acid, 3-(5-((2,3-difluoro-6-methoxyphenyl)methoxy)-2-fluoro-4-methoxyphenyl)-1,2,3,4-tetrahydro-2,4-dioxo-

11. 3-(5-((2,3-difluoro-6-methoxyphenyl)methoxy)-2-fluoro-4-methoxyphenyl)-2,4-dioxo-1,2,3,4-tetrahydrothieno(3,4-d)pyrimidine-5-carboxylic Acid

12. Linzagolix (usan/inn)

13. Linzagolix [usan:inn]

14. Unii-7cdw97huex

15. Linzagolix [who-dd]

16. Schembl2333748

17. Chembl3668014

18. Bdbm160329

19. Dtxsid801337395

20. Bcp30444

21. Who 10711

22. Hy-109093

23. D11608

24. Us9040693, 233

25. 3-[5-(2,3-difluoro-6-methoxybenzyloxy)-2-fluoro-4-methoxyphenyl]-2,4-dioxo-1,2,3,4-tetrahydrothieno[3,4-d]pyrimidine-5-carboxylic Acid

26. 3-[5-[(2,3-difluoro-6-methoxyphenyl)methoxy]-2-fluoro-4-methoxyphenyl]-2,4-dioxo-1h-thieno[3,4-d]pyrimidine-5-carboxylic Acid

2.4 Create Date
2007-08-09
3 Chemical and Physical Properties
Molecular Weight 508.4 g/mol
Molecular Formula C22H15F3N2O7S
XLogP33.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count11
Rotatable Bond Count7
Exact Mass508.05520648 g/mol
Monoisotopic Mass508.05520648 g/mol
Topological Polar Surface Area143 Ų
Heavy Atom Count35
Formal Charge0
Complexity826
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 ATC Code

H - Systemic hormonal preparations, excl. sex hormones and insulins

H01 - Pituitary and hypothalamic hormones and analogues

H01C - Hypothalamic hormones

H01CC - Anti-gonadotropin-releasing hormones

H01CC04 - Linzagolix


API SUPPLIERS

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Moehs Iberica

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Chongqing Sintaho Pharmaceutical

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Maithri Drugs

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Virtual BoothMoehs Group, a reference company in the production of pharmaceutical active ingredients.

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Linzagolix

About the Company : Since its founding in 1962, MOEHS has produced Active Pharmaceutical Ingredients (APIs) for the international pharmaceutical industry. Thanks to a business history of more than 50 ...

Since its founding in 1962, MOEHS has produced Active Pharmaceutical Ingredients (APIs) for the international pharmaceutical industry. Thanks to a business history of more than 50 years, MOEHS has considerable technical experience in the production of these substances. At Moehs Group we have a large tradition and experience in the area of manufacturing of active pharmaceutical and veterinary ingredients, agrochemicals, nutraceutical, cosmetic, as well as fine chemistry in general, with high levels of quality and safety standards-GMP´s, ICH, approved by the FDA and TGA.
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Aspen API

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About the Company : Aspen API is the cooperative entity formed by Aspen Oss in the Netherlands and Fine Chemicals Corporation in South Africa. With quality, compliance, and teamwork at its core, Aspen...

Aspen API is the cooperative entity formed by Aspen Oss in the Netherlands and Fine Chemicals Corporation in South Africa. With quality, compliance, and teamwork at its core, Aspen API works tirelessly to deliver top-quality APIs to clients worldwide. Aspen API has a portfolio of over 58 high-quality APIs, including high potency, oncology, peptides, narcotics, analgesics, botanical extractions, and biochemicals. Aspen API places a strong emphasis on sustainability. It employs eco-friendly technologies and solvents in its chemical processes, ensuring responsible and environmentally conscious manufacturing.
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About the Company :

Established in 2004, Metrochem API is one of the fastest-growing APIs, pellets & intermediates manufacturers. It has 6 dedicated manufacturing facilities for its 3 core product ...

Established in 2004, Metrochem API is one of the fastest-growing APIs, pellets & intermediates manufacturers. It has 6 dedicated manufacturing facilities for its 3 core product groups and has been approved by ISO 9001-2015, USFDA, WHO GMP, Cofepris & Japanese authorities. Metrochem’s in-depth industry knowledge, & hi-tech & advanced infrastructure, helps it provide quality products to its customers. Note: None of the products will be supplied to the countries where this could conflict with existing patents. Further, any products under patent will be offered for R&D purposes only. However, the final responsibility lies with the buyer
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About the Company : Sintaho Pharmaceutical Co., Ltd., located in Chongqing, China, contributes to being the most dependable partner for global pharmaceutical companies. Sintaho specializes in chemosyn...

Sintaho Pharmaceutical Co., Ltd., located in Chongqing, China, contributes to being the most dependable partner for global pharmaceutical companies. Sintaho specializes in chemosynthetic APIs (application contains oncology, nervous system, and metabolic diseases and etc.,) with a product portfolio ranging from small molecule APIs, ADC compounds (linkers and payloads) to polypeptides, also provides CDMO services of cytotoxic and OEB4/5 grade APIs.
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Linzagolix

About the Company : Maithri Drugs is one of India's fast-growing pharmaceutical companies. Maithri's strategic focus is on active pharma ingredients (APIs). The company is widely recognized for its ex...

Maithri Drugs is one of India's fast-growing pharmaceutical companies. Maithri's strategic focus is on active pharma ingredients (APIs). The company is widely recognized for its excellent research & development and aggressive growth strategies. Our 32 US DMFs and 9 CEPs in a short span attest to our R&D excellence. Maithri's manufacturing facility is located in Hyderabad. This facility is audited and approved by the US FDA. In addition, our facility is certified according to the standards of DCGI, WHO GMP, and ISO 9001:2015 We have a portfolio of 65 products and are continually expanding.
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Linzagolix

About the Company : Sandoo Pharmaceuticals and Chemcials Co.,Ltd was established in 2009, with a young and active team, located in Ningbo, China. Specializes in exporting and importing pharmaceutica...

Sandoo Pharmaceuticals and Chemcials Co.,Ltd was established in 2009, with a young and active team, located in Ningbo, China. Specializes in exporting and importing pharmaceutical intermediates and chemical products as well as active pharmaceutical ingredients.
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Linzagolix

About the Company : Wuhan Sun-shine chemical Corporation Limited (Shanghai Sun-shine Chemical Technology Corporation Limited) is a high-tech enterprise engaged inR&D and sales of related compounds of ...

Wuhan Sun-shine chemical Corporation Limited (Shanghai Sun-shine Chemical Technology Corporation Limited) is a high-tech enterprise engaged inR&D and sales of related compounds of new drugs, specialty pharmaceutical API, advanced intermediates, organic synthetic masonry, and high-end reagents, etc. The special services we provide include: the technical development of chiral drugs, the development of an active molecular library. Sun-shine chemical has over 1,500m² of operation premises. The R&D laboratory is more than 1,000m² and is equipped with a variety of R&D laboratory equipment.
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Drugs in Development

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Details:

Yselty® (linzagolix) is the first and only approved GnRH antagonist to provide flexible dosing options with and without hormonal add-back therapy, for the Treatment of Uterine Fibroids.


Lead Product(s): Linzagolix

Therapeutic Area: Obstetrics/Gynecology (Women’s Health) Brand Name: Yselty

Study Phase: ApprovedProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable June 28, 2022

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01

ObsEva

Switzerland
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euroPLX 86 Munich
Not Confirmed

ObsEva

Switzerland
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euroPLX 86 Munich
Not Confirmed

Details : Yselty® (linzagolix) is the first and only approved GnRH antagonist to provide flexible dosing options with and without hormonal add-back therapy, for the Treatment of Uterine Fibroids.

Brand Name : Yselty

Molecule Type : Small molecule

Upfront Cash : Not Applicable

June 28, 2022

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Details:

Yselty (Linzagolix) is the only approved oral GnRH antagonist to offer flexible dosing options, with and without additional hormonal therapy, for women suffering from UF.


Lead Product(s): Linzagolix

Therapeutic Area: Obstetrics/Gynecology (Women’s Health) Brand Name: Yselty

Study Phase: ApprovedProduct Type: Small molecule

Sponsor: Theramex

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable June 17, 2022

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02

ObsEva

Switzerland
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euroPLX 86 Munich
Not Confirmed

ObsEva

Switzerland
arrow
euroPLX 86 Munich
Not Confirmed

Details : Yselty (Linzagolix) is the only approved oral GnRH antagonist to offer flexible dosing options, with and without additional hormonal therapy, for women suffering from UF.

Brand Name : Yselty

Molecule Type : Small molecule

Upfront Cash : Not Applicable

June 17, 2022

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Details:

Summary of data and key takeaway: At 12 weeks, once-daily treatment with Yselty (linzagolix 200 mg) with hormonal ABT significantly improved dysmenorrhea, non-menstrual pelvic pain, and other symptoms of endometriosis, including dyschezia and ability to do daily activities.


Lead Product(s): Linzagolix

Therapeutic Area: Obstetrics/Gynecology (Women’s Health) Brand Name: Yselty

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable May 24, 2022

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03

ObsEva

Switzerland
arrow
euroPLX 86 Munich
Not Confirmed

ObsEva

Switzerland
arrow
euroPLX 86 Munich
Not Confirmed

Details : Summary of data and key takeaway: At 12 weeks, once-daily treatment with Yselty (linzagolix 200 mg) with hormonal ABT significantly improved dysmenorrhea, non-menstrual pelvic pain, and other symptoms of endometriosis, including dyschezia and ability to ...

Brand Name : Yselty

Molecule Type : Small molecule

Upfront Cash : Not Applicable

May 24, 2022

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Details:

Results demonstrated that OBE-2109 (linzagolix) has potential to balance safety, efficacy, and address wide-ranging symptoms of uterine fibroids also showed promise in delivering sustained clinical benefit.


Lead Product(s): Linzagolix,Estradiol,Norethisterone Acetate

Therapeutic Area: Obstetrics/Gynecology (Women’s Health) Brand Name: OBE-2109

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable May 09, 2022

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04

ObsEva

Switzerland
arrow
euroPLX 86 Munich
Not Confirmed

ObsEva

Switzerland
arrow
euroPLX 86 Munich
Not Confirmed

Details : Results demonstrated that OBE-2109 (linzagolix) has potential to balance safety, efficacy, and address wide-ranging symptoms of uterine fibroids also showed promise in delivering sustained clinical benefit.

Brand Name : OBE-2109

Molecule Type : Small molecule

Upfront Cash : Not Applicable

May 09, 2022

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Details:

ObsEva has entered into a licensing agreement with Theramex to support the commercialization and market introduction of linzagolix in Europe. Theramex’s extensive women’s health commercial infrastructure includes a dedicated sales force of more than 180 representatives.


Lead Product(s): Linzagolix

Therapeutic Area: Obstetrics/Gynecology (Women’s Health) Brand Name: OBE-2109

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: Theramex

Deal Size: Undisclosed Upfront Cash: Undisclosed

Deal Type: Licensing Agreement April 25, 2022

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05

ObsEva

Switzerland
arrow
euroPLX 86 Munich
Not Confirmed

ObsEva

Switzerland
arrow
euroPLX 86 Munich
Not Confirmed

Details : ObsEva has entered into a licensing agreement with Theramex to support the commercialization and market introduction of linzagolix in Europe. Theramex’s extensive women’s health commercial infrastructure includes a dedicated sales force of more than ...

Brand Name : OBE-2109

Molecule Type : Small molecule

Upfront Cash : Undisclosed

April 25, 2022

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Details:

Both DYS and NMPP showed rapid reductions compared to placebo (after 1 and 2 months of treatment), with continued reduction up to 6 months of treatment and with higher reductions with linzagolix, an oral GnRH antagonist, 200 mg + ABT compared to linzagolix 75 mg.


Lead Product(s): Linzagolix,Estradiol,Norethisterone Acetate

Therapeutic Area: Obstetrics/Gynecology (Women’s Health) Brand Name: OBE-2109

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable March 22, 2022

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06

ObsEva

Switzerland
arrow
euroPLX 86 Munich
Not Confirmed

ObsEva

Switzerland
arrow
euroPLX 86 Munich
Not Confirmed

Details : Both DYS and NMPP showed rapid reductions compared to placebo (after 1 and 2 months of treatment), with continued reduction up to 6 months of treatment and with higher reductions with linzagolix, an oral GnRH antagonist, 200 mg + ABT compared to linzago...

Brand Name : OBE-2109

Molecule Type : Small molecule

Upfront Cash : Not Applicable

March 22, 2022

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Details:

Linzagolix is a GnRH receptor antagonist for the treatment of uterine fibroids. Linzagolix is also in development as a potential treatment for endometriosis-associated pain. Linzagolix is not currently approved for any indication anywhere in the world.


Lead Product(s): Linzagolix

Therapeutic Area: Obstetrics/Gynecology (Women’s Health) Brand Name: Undisclosed

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: ObsEva

Deal Size: Undisclosed Upfront Cash: Undisclosed

Deal Type: Licensing Agreement February 10, 2022

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07

Theramex

United Kingdom
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euroPLX 86 Munich
Not Confirmed

Theramex

United Kingdom
arrow
euroPLX 86 Munich
Not Confirmed

Details : Linzagolix is a GnRH receptor antagonist for the treatment of uterine fibroids. Linzagolix is also in development as a potential treatment for endometriosis-associated pain. Linzagolix is not currently approved for any indication anywhere in the world.

Brand Name : Undisclosed

Molecule Type : Small molecule

Upfront Cash : Undisclosed

February 10, 2022

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Details:

The data from the Phase 3 PRIMROSE studies of Yselty (linzagolix) for the treatment of uterine fibroids demonstrating sustained safety and efficacy results at 52 weeks.


Lead Product(s): Linzagolix

Therapeutic Area: Obstetrics/Gynecology (Women’s Health) Brand Name: Yselty

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable December 10, 2021

blank

08

ObsEva

Switzerland
arrow
euroPLX 86 Munich
Not Confirmed

ObsEva

Switzerland
arrow
euroPLX 86 Munich
Not Confirmed

Details : The data from the Phase 3 PRIMROSE studies of Yselty (linzagolix) for the treatment of uterine fibroids demonstrating sustained safety and efficacy results at 52 weeks.

Brand Name : Yselty

Molecule Type : Small molecule

Upfront Cash : Not Applicable

December 10, 2021

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Details:

Study on trial of Linzagolix investigated that efficacy and safety of two dosing regimens, 100mg once daily and 200mg once daily, alone or in combination with hormonal ABT for the treatment of heavy menstrual bleeding associated with uterine fibroids.


Lead Product(s): Linzagolix

Therapeutic Area: Obstetrics/Gynecology (Women’s Health) Brand Name: Undisclosed

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable November 22, 2021

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09

ObsEva

Switzerland
arrow
euroPLX 86 Munich
Not Confirmed

ObsEva

Switzerland
arrow
euroPLX 86 Munich
Not Confirmed

Details : Study on trial of Linzagolix investigated that efficacy and safety of two dosing regimens, 100mg once daily and 200mg once daily, alone or in combination with hormonal ABT for the treatment of heavy menstrual bleeding associated with uterine fibroids.

Brand Name : Undisclosed

Molecule Type : Small molecule

Upfront Cash : Not Applicable

November 22, 2021

blank

Details:

Linzagolix is the only GnRH antagonist to provide flexible dosing options to better address the individual needs of patients, and the results further underscore its differentiated profile and potential clinical utility.


Lead Product(s): Linzagolix

Therapeutic Area: Obstetrics/Gynecology (Women’s Health) Brand Name: Yselty

Study Phase: Phase IIIProduct Type: Small molecule

Sponsor: Not Applicable

Deal Size: Not Applicable Upfront Cash: Not Applicable

Deal Type: Not Applicable October 20, 2021

blank

10

ObsEva

Switzerland
arrow
euroPLX 86 Munich
Not Confirmed

ObsEva

Switzerland
arrow
euroPLX 86 Munich
Not Confirmed

Details : Linzagolix is the only GnRH antagonist to provide flexible dosing options to better address the individual needs of patients, and the results further underscore its differentiated profile and potential clinical utility.

Brand Name : Yselty

Molecule Type : Small molecule

Upfront Cash : Not Applicable

October 20, 2021

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INTERMEDIATES SUPPLIERS

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PMC Isochem

France
BioFlorida Conference
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Virtual BoothPMC Isochem is your partner for smart CDMOs of Intermediates, APIs, & excipients & a catalog of Intermediates & Generic APIs.

CAS Number : 187543-87-9

End Use API : Linzagolix

About The Company : PMC Isochem is a CDMO company acquired by PMC International in 2017. It manufactures cGMP intermediates, active pharmaceutical ingredients and functional excipi...

PMC Isochem
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NEWS #PharmaBuzz

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https://www.fdanews.com/articles/208842-obseva-scraps-plans-for-uterine-fibroid-candidate?v=preview

FDANEWS
02 Aug 2022

https://www.fiercepharma.com/pharma/ominous-fda-talks-obseva-scraps-lead-womens-health-drug-plots-layoffs-major-restructuring

Angus Liu FIERCEPHARMA
28 Jul 2022

https://www.globenewswire.com/news-release/2022/06/28/2470795/0/en/ObsEva-Announces-UK-MHRA-Marketing-Authorization-for-Yselty-linzagolix-an-Oral-GnRH-Antagonist-for-the-Treatment-of-Uterine-Fibroids.html

GLOBENEWSWIRE
28 Jun 2022

https://www.businesswire.com/news/home/20220617005176/en

BUSINESSWIRE
17 Jun 2022

https://www.globenewswire.com/news-release/2022/05/25/2449884/0/en/ObsEva-Presents-Clinical-Data-on-Oral-GnRH-Antagonist-Linzagolix-at-Multiple-Congresses.html

GLOBENEWSWIRE
25 May 2022

https://www.globenewswire.com/news-release/2022/04/25/2427956/0/en/ObsEva-Announces-Confirmation-of-Positive-CHMP-Opinion-for-Linzagolix-an-Oral-GnRH-Antagonist-for-the-Treatment-of-Uterine-Fibroids.html

GLOBENEWSWIRE
25 Apr 2022

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