CA2953722C - Crystalline (3z,5s)-5-(hydroxymethyl)-1-[(2'-methyl-1,1'-biphenyl-4-yl)carbonyl]pyrrolidin-3-one o-methyloxime, and methods of using the same - Google Patents
Crystalline (3z,5s)-5-(hydroxymethyl)-1-[(2'-methyl-1,1'-biphenyl-4-yl)carbonyl]pyrrolidin-3-one o-methyloxime, and methods of using the same Download PDFInfo
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- CA2953722C CA2953722C CA2953722A CA2953722A CA2953722C CA 2953722 C CA2953722 C CA 2953722C CA 2953722 A CA2953722 A CA 2953722A CA 2953722 A CA2953722 A CA 2953722A CA 2953722 C CA2953722 C CA 2953722C
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- Prior art keywords
- crystalline compound
- methyloxime
- hydroxymethyl
- pyrrolidin
- biphenyl
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- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- UEHLXXJAWYWUGI-UHFFFAOYSA-M nitromersol Chemical compound CC1=CC=C([N+]([O-])=O)C2=C1O[Hg]2 UEHLXXJAWYWUGI-UHFFFAOYSA-M 0.000 description 1
- 229940118238 nitromersol Drugs 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
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- 201000006195 perinatal necrotizing enterocolitis Diseases 0.000 description 1
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- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229940096826 phenylmercuric acetate Drugs 0.000 description 1
- 230000001817 pituitary effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
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- 210000000063 presynaptic terminal Anatomy 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 208000005333 pulmonary edema Diseases 0.000 description 1
- 208000002815 pulmonary hypertension Diseases 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
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- 230000002040 relaxant effect Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000003938 response to stress Effects 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 229960000371 rofecoxib Drugs 0.000 description 1
- RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 description 1
- 229960002052 salbutamol Drugs 0.000 description 1
- 230000036332 sexual response Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229940083037 simethicone Drugs 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 229960001790 sodium citrate Drugs 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
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- UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide pyridine complex Chemical compound O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 1
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- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
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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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/04—Drugs for genital or sexual disorders; Contraceptives for inducing labour or abortion; Uterotonics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/06—Antiabortive agents; Labour repressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/10—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Epidemiology (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462020076P | 2014-07-02 | 2014-07-02 | |
| US62/020,076 | 2014-07-02 | ||
| PCT/EP2015/062881 WO2016000920A1 (en) | 2014-07-02 | 2015-06-10 | Crystalline (3z,5s)-5-(hydroxymethyl)-1-[(2'-methyl-1,1'-biphenyl-4-yl)carbonyl]pyrrolidin-3-one o-methyloxime useful in methods of treating conditions related to the ot-r activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2953722A1 CA2953722A1 (en) | 2016-01-07 |
| CA2953722C true CA2953722C (en) | 2022-09-13 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2953722A Active CA2953722C (en) | 2014-07-02 | 2015-06-10 | Crystalline (3z,5s)-5-(hydroxymethyl)-1-[(2'-methyl-1,1'-biphenyl-4-yl)carbonyl]pyrrolidin-3-one o-methyloxime, and methods of using the same |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US9718772B2 (enExample) |
| EP (2) | EP3753921A1 (enExample) |
| JP (4) | JP2017519015A (enExample) |
| KR (1) | KR102470283B1 (enExample) |
| CN (3) | CN106795110A (enExample) |
| AU (1) | AU2015283133B2 (enExample) |
| CA (1) | CA2953722C (enExample) |
| EA (2) | EA031353B1 (enExample) |
| ES (1) | ES2774789T3 (enExample) |
| IL (1) | IL249652B (enExample) |
| MX (1) | MX371068B (enExample) |
| UA (1) | UA122210C2 (enExample) |
| WO (1) | WO2016000920A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2845850A1 (en) | 2013-09-10 | 2015-03-11 | ObsEva S.A. | Pyrrolidine derivatives as oxytocin/vasopressin V1a receptors antagonists |
| EP2886107A1 (en) | 2013-12-17 | 2015-06-24 | ObsEva S.A. | Oral formulations of pyrrolydine derivatives |
| UA122210C2 (uk) | 2014-07-02 | 2020-10-12 | Обсева С.А. | Кристалічний о-метилоксим (3z,5s)-5-(гідроксиметил)-1-[(2'-метил-1,1'-біфеніл-4-іл)карбоніл]піролідин-3-oну, корисний у способах лікування станів, пов'язаних з активністю ot-r |
| AU2017205254B2 (en) | 2016-01-04 | 2021-05-20 | Xoma (Us) Lcc | Alpha-amino esters of hydroxypropylthiazolidine carboxamide derivative and salt form, crystal polymorph thereof |
| WO2018015497A2 (en) | 2016-07-21 | 2018-01-25 | ObsEva S.A. | Oxytocin antagonist dosing regimens for promoting embryo implantation and preventing miscarriage |
| CN114667141A (zh) * | 2019-09-03 | 2022-06-24 | 奥布赛瓦股份公司 | 用于促进胚胎移植和预防流产的催产素拮抗剂给药方案 |
| JP7083793B2 (ja) * | 2019-09-10 | 2022-06-13 | Ｊｆｅケミカル株式会社 | パラターフェニルテトラカルボン酸およびパラターフェニルテトラカルボン酸二無水物の製造方法 |
| WO2021160597A1 (en) | 2020-02-10 | 2021-08-19 | ObsEva S.A. | Biomarkers for oxytocin receptor antagonist therapy |
| EP4313061A4 (en) * | 2021-03-31 | 2025-03-05 | The Board of Trustees of the Leland Stanford Junior University | FORMULATIONS FOR PROLONGATION OF GESTATION AND FOR COMPLICATIONS OF MENSTRUATION OR GESTATION |
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| YU120988A (en) | 1988-06-23 | 1990-06-30 | Lek Tovarna Farmacevtskih | Process for preparing new dispersion pills of cimetidine |
| YU183988A (en) | 1988-09-30 | 1990-08-31 | Lek Tovarna Farmacevtskih | Process for preparing dispersion pills of dihydroergotoxine |
| JP2927532B2 (ja) | 1989-11-09 | 1999-07-28 | 塩野義製薬株式会社 | 含窒素異項環オキシーフェノキシ酢酸誘導体およびその除草剤としての用途 |
| US5889001A (en) | 1993-07-29 | 1999-03-30 | American Cyanamid Company | Tricyclic diazepine vasopressin antagonists and oxytocin antagonists |
| JP3534903B2 (ja) | 1995-06-09 | 2004-06-07 | 鐘淵化学工業株式会社 | １−［３−クロロ−（２ｓ）−メチルプロピオニル］−ピロリジン−（２ｓ）−カルボン酸の製造方法 |
| GB9603699D0 (en) | 1996-02-21 | 1996-04-17 | Boots Co Plc | Therapeutic composition |
| US6696484B2 (en) | 1997-10-31 | 2004-02-24 | University Of Chicago Office Of Technology And Intellectual Property | Method and compositions for regulation of 5-alpha reductase activity |
| US6329418B1 (en) | 1998-04-14 | 2001-12-11 | The Procter & Gamble Company | Substituted pyrrolidine hydroxamate metalloprotease inhibitors |
| HK1046644B (en) | 1999-12-09 | 2006-11-10 | Reckitt Benckiser Healthcare (Uk) Limited | Compressed tablet composition comprising a nsaid |
| PT1268418E (pt) | 2000-03-27 | 2006-08-31 | Applied Research Systems | Derivados da pirrolidina farmacologicamente activos com inibidores bax |
| HRP20020705A2 (en) | 2000-03-27 | 2004-12-31 | Applied Research Systems | Pharmaceutically active pyrrolidine derivatives |
| TW536751B (en) | 2000-07-14 | 2003-06-11 | Nitto Denko Corp | Cleaning sheet, conveying member using the same, and substrate processing equipment cleaning method using them |
| DE60226431D1 (de) | 2001-03-20 | 2008-06-19 | Serono Lab | Pyrrolidinesterderivate mit oxytocinmodulierender wirkung |
| KR200245627Y1 (ko) * | 2001-05-15 | 2001-10-15 | 김병두 | 전기 가열부재가 부착된 냄비 |
| CA2449578C (en) | 2001-06-18 | 2011-12-13 | Applied Research Systems Ars Holding N.V. | Pyrrolidine oxadiazole- and thiadiazole derivatives |
| JP2003192582A (ja) | 2001-12-12 | 2003-07-09 | Merck Patent Gmbh | ナプロキセンナトリウムを含む速放性錠剤 |
| UA78058C2 (en) | 2002-07-05 | 2007-02-15 | Applied Research Systems | Pyrrolidine derivative as oxitocin antagonists |
| ATE449067T1 (de) | 2003-02-27 | 2009-12-15 | Merck Serono Sa | Pyrrolidin-derivate als oxytocin antagonisten |
| EA011026B1 (ru) | 2004-02-26 | 2008-12-30 | Лаборатуар Сероно Са | Способ получения пирролидиноксимов |
| GB2411355B (en) | 2004-02-27 | 2006-02-22 | Niche Generics Ltd | Pharmaceutical composition |
| MX2007014022A (es) | 2005-05-10 | 2008-02-07 | Ferring Int Ct Sa | Uso de antagonistas de oxitocina y/o vasopresina en la reproduccion asistida. |
| JP2008189732A (ja) | 2007-02-01 | 2008-08-21 | Fujifilm Corp | セルロースアシレート組成物、セルロースアシレートフィルム、光学補償シート、偏光板および液晶表示装置 |
| PL2572705T3 (pl) | 2007-10-01 | 2018-01-31 | Lesvi Laboratorios Sl | Tabletki ulegające rozpadowi w jamie ustnej |
| US9201077B2 (en) | 2009-07-27 | 2015-12-01 | Colorado State University Research Foundation | Direct enzyme immunoassay for measurement of serum progesterone levels |
| CA2892000A1 (en) | 2012-11-26 | 2014-05-30 | Piotr Pierzynski | Method and system for diagnosing uterine contraction levels using image analysis |
| EP2845850A1 (en) | 2013-09-10 | 2015-03-11 | ObsEva S.A. | Pyrrolidine derivatives as oxytocin/vasopressin V1a receptors antagonists |
| EP2886107A1 (en) * | 2013-12-17 | 2015-06-24 | ObsEva S.A. | Oral formulations of pyrrolydine derivatives |
| UA122210C2 (uk) | 2014-07-02 | 2020-10-12 | Обсева С.А. | Кристалічний о-метилоксим (3z,5s)-5-(гідроксиметил)-1-[(2'-метил-1,1'-біфеніл-4-іл)карбоніл]піролідин-3-oну, корисний у способах лікування станів, пов'язаних з активністю ot-r |
| EP3501533B1 (en) | 2014-12-22 | 2025-07-09 | Ferring B.V. | Obe001 for use in the treatment in implantation and pregnancy in women undergoing assisted reproductive technologies |
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2015
- 2015-06-10 UA UAA201700678A patent/UA122210C2/uk unknown
- 2015-06-10 EA EA201790080A patent/EA031353B1/ru unknown
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2022
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2024
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| AU2015283133B2 (en) | 2019-05-16 |
| KR102470283B1 (ko) | 2022-11-23 |
| EA201891873A1 (ru) | 2019-04-30 |
| EP3164384B1 (en) | 2019-12-04 |
| ES2774789T3 (es) | 2020-07-22 |
| US9718772B2 (en) | 2017-08-01 |
| US10752583B2 (en) | 2020-08-25 |
| EP3753921A1 (en) | 2020-12-23 |
| WO2016000920A1 (en) | 2016-01-07 |
| US20170320822A1 (en) | 2017-11-09 |
| EA201790080A1 (ru) | 2017-06-30 |
| JP2017519015A (ja) | 2017-07-13 |
| CN106795110A (zh) | 2017-05-31 |
| IL249652B (en) | 2021-09-30 |
| CN114105850A (zh) | 2022-03-01 |
| MX2016016751A (es) | 2017-08-08 |
| US20160002160A1 (en) | 2016-01-07 |
| AU2015283133A1 (en) | 2017-02-16 |
| MX371068B (es) | 2020-01-15 |
| IL249652A0 (en) | 2017-02-28 |
| EP3164384A1 (en) | 2017-05-10 |
| UA122210C2 (uk) | 2020-10-12 |
| EA031353B1 (ru) | 2018-12-28 |
| CA2953722A1 (en) | 2016-01-07 |
| JP2023018037A (ja) | 2023-02-07 |
| CN114105851A (zh) | 2022-03-01 |
| KR20170023961A (ko) | 2017-03-06 |
| JP2025013885A (ja) | 2025-01-28 |
| JP2021038236A (ja) | 2021-03-11 |
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