ZA200409820B - Pyrrolidine derivatives as oxytocin antagonists - Google Patents
Pyrrolidine derivatives as oxytocin antagonists Download PDFInfo
- Publication number
- ZA200409820B ZA200409820B ZA200409820A ZA200409820A ZA200409820B ZA 200409820 B ZA200409820 B ZA 200409820B ZA 200409820 A ZA200409820 A ZA 200409820A ZA 200409820 A ZA200409820 A ZA 200409820A ZA 200409820 B ZA200409820 B ZA 200409820B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- pyrrolidin
- biphenyl
- ylcarbonyl
- heteroaryl
- Prior art date
Links
- 150000003235 pyrrolidines Chemical class 0.000 title description 16
- 239000003336 oxytocin antagonist Substances 0.000 title description 6
- 229940121361 oxytocin antagonists Drugs 0.000 title description 6
- 208000006399 Premature Obstetric Labor Diseases 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 208000005171 Dysmenorrhea Diseases 0.000 claims abstract description 15
- 206010013935 Dysmenorrhoea Diseases 0.000 claims abstract description 14
- FKCMADOPPWWGNZ-YUMQZZPRSA-N [(2r)-1-[(2s)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CC(C)[C@H](N)C(=O)N1CCC[C@H]1B(O)O FKCMADOPPWWGNZ-YUMQZZPRSA-N 0.000 claims abstract description 14
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 12
- 208000005107 Premature Birth Diseases 0.000 claims abstract description 11
- 206010036590 Premature baby Diseases 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 230000002265 prevention Effects 0.000 claims abstract description 8
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 4
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- 229960001723 oxytocin Drugs 0.000 claims description 26
- XNOPRXBHLZRZKH-DSZYJQQASA-N oxytocin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@H](N)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 XNOPRXBHLZRZKH-DSZYJQQASA-N 0.000 claims description 21
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 18
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- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000010318 polygalacturonic acid Substances 0.000 description 1
- 229920002643 polyglutamic acid Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229960002052 salbutamol Drugs 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960000195 terbutaline Drugs 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003555 thioacetals Chemical class 0.000 description 1
- 229940125712 tocolytic agent Drugs 0.000 description 1
- 239000003675 tocolytic agent Substances 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 230000001228 trophic effect Effects 0.000 description 1
- 230000003827 upregulation Effects 0.000 description 1
- 229960003726 vasopressin Drugs 0.000 description 1
- 239000003038 vasopressin antagonist Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- A61P15/06—Antiabortive agents; Labour repressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Diabetes (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02100784 | 2002-07-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200409820B true ZA200409820B (en) | 2006-07-26 |
Family
ID=30011225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200409820A ZA200409820B (en) | 2002-07-05 | 2004-12-03 | Pyrrolidine derivatives as oxytocin antagonists |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US7115754B2 (de) |
| EP (1) | EP1532109B1 (de) |
| JP (1) | JP4851085B2 (de) |
| CN (1) | CN1330633C (de) |
| AT (1) | ATE442354T1 (de) |
| BR (1) | BR0312586A (de) |
| CA (1) | CA2487532C (de) |
| DE (1) | DE60329189D1 (de) |
| EA (1) | EA008479B1 (de) |
| ES (1) | ES2330841T3 (de) |
| HK (1) | HK1076107A1 (de) |
| HR (1) | HRP20041208A2 (de) |
| IL (1) | IL166103A0 (de) |
| MX (1) | MXPA05000326A (de) |
| NO (1) | NO20050612L (de) |
| PL (1) | PL374666A1 (de) |
| RS (1) | RS115804A (de) |
| UA (1) | UA78058C2 (de) |
| WO (1) | WO2004005249A1 (de) |
| ZA (1) | ZA200409820B (de) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ20033475A3 (en) * | 2001-06-18 | 2004-05-12 | Appliedáresearchásystemsáarsáholdingán@V | Pyrrolidine oxadiazole- and thiadiazole oxime derivatives being oxytocin receptor antagonists. |
| US10722645B2 (en) | 2011-12-21 | 2020-07-28 | Deka Products Limited Partnership | Syringe pump, and related method and system |
| EP2845850A1 (de) * | 2013-09-10 | 2015-03-11 | ObsEva S.A. | Pyrrolidinderivate als Oxytocin/Vasopressin-V1a-Rezeptorantagonisten |
| EP2886107A1 (de) * | 2013-12-17 | 2015-06-24 | ObsEva S.A. | Orale Formulierungen von Pyrrolydinderivaten |
| CN106795110A (zh) * | 2014-07-02 | 2017-05-31 | 奥布赛瓦股份公司 | 治疗ot‑r活性相关的病症的方法中可用的晶体(3z，5s)‑5‑(羟甲基)‑1‑[(2’‑甲基‑1，1’‑联苯‑4‑基)羰基]吡咯烷‑3‑酮o‑甲基肟 |
| EP3037101B1 (de) | 2014-12-22 | 2019-03-06 | Ferring B.V. | Oxytocinrezeptorantagonistentherapie in der Lutealphase für Implantation und Schwangerschaft bei mit Technologien zur unterstützten Fortpflanzung behandelten Frauen |
| IL284912B (en) | 2016-01-04 | 2022-07-01 | Merck Serono Sa | L-Valinate derivative of hydroxypropylthiazolidine carboxamide and salt form, crystalline polymorph thereof |
| CA3031252A1 (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 |
| US20230102503A1 (en) | 2020-02-10 | 2023-03-30 | ObsEva S.A. | Biomarkers for oxytocin receptor antagonist therapy |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6329418B1 (en) | 1998-04-14 | 2001-12-11 | The Procter & Gamble Company | Substituted pyrrolidine hydroxamate metalloprotease inhibitors |
| ES2261404T3 (es) * | 2000-03-27 | 2006-11-16 | Applied Research Systems Ars Holding N.V. | Derivados de pirrolidina utiles como inhibidores de bax. |
-
2003
- 2003-04-07 UA UA20041210895A patent/UA78058C2/uk unknown
- 2003-07-04 RS YUP-1158/04A patent/RS115804A/sr unknown
- 2003-07-04 BR BR0312586-6A patent/BR0312586A/pt not_active IP Right Cessation
- 2003-07-04 WO PCT/EP2003/050286 patent/WO2004005249A1/en active Application Filing
- 2003-07-04 ES ES03762692T patent/ES2330841T3/es not_active Expired - Lifetime
- 2003-07-04 US US10/518,543 patent/US7115754B2/en not_active Expired - Lifetime
- 2003-07-04 PL PL03374666A patent/PL374666A1/xx not_active Application Discontinuation
- 2003-07-04 DE DE60329189T patent/DE60329189D1/de not_active Expired - Lifetime
- 2003-07-04 EA EA200500133A patent/EA008479B1/ru not_active IP Right Cessation
- 2003-07-04 JP JP2004518783A patent/JP4851085B2/ja not_active Expired - Fee Related
- 2003-07-04 CA CA2487532A patent/CA2487532C/en not_active Expired - Fee Related
- 2003-07-04 CN CNB038204010A patent/CN1330633C/zh not_active Expired - Fee Related
- 2003-07-04 AT AT03762692T patent/ATE442354T1/de not_active IP Right Cessation
- 2003-07-04 EP EP03762692A patent/EP1532109B1/de not_active Expired - Lifetime
- 2003-07-04 MX MXPA05000326A patent/MXPA05000326A/es active IP Right Grant
-
2004
- 2004-12-03 ZA ZA200409820A patent/ZA200409820B/en unknown
- 2004-12-23 HR HR20041208A patent/HRP20041208A2/xx not_active Application Discontinuation
-
2005
- 2005-01-03 IL IL16610305A patent/IL166103A0/xx unknown
- 2005-02-03 NO NO20050612A patent/NO20050612L/no not_active Application Discontinuation
- 2005-11-17 HK HK05110274A patent/HK1076107A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2487532A1 (en) | 2004-01-15 |
| CN1330633C (zh) | 2007-08-08 |
| EP1532109B1 (de) | 2009-09-09 |
| UA78058C2 (en) | 2007-02-15 |
| CN1678576A (zh) | 2005-10-05 |
| US20060004020A1 (en) | 2006-01-05 |
| CA2487532C (en) | 2011-03-08 |
| DE60329189D1 (de) | 2009-10-22 |
| AU2003254498A1 (en) | 2004-01-23 |
| IL166103A0 (en) | 2006-01-15 |
| US7115754B2 (en) | 2006-10-03 |
| ATE442354T1 (de) | 2009-09-15 |
| RS115804A (en) | 2007-02-05 |
| NO20050612L (no) | 2005-02-03 |
| EA008479B1 (ru) | 2007-06-29 |
| PL374666A1 (en) | 2005-10-31 |
| ES2330841T3 (es) | 2009-12-16 |
| HK1076107A1 (en) | 2006-01-06 |
| EA200500133A1 (ru) | 2005-08-25 |
| WO2004005249A1 (en) | 2004-01-15 |
| HRP20041208A2 (en) | 2005-06-30 |
| JP2005533828A (ja) | 2005-11-10 |
| BR0312586A (pt) | 2005-04-12 |
| MXPA05000326A (es) | 2005-03-31 |
| JP4851085B2 (ja) | 2012-01-11 |
| EP1532109A1 (de) | 2005-05-25 |
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