ZA200401459B - Glycine-substituted thieno[2,3-d]pyrimidines with combined LH and FSH agonistic activity. - Google Patents
Glycine-substituted thieno[2,3-d]pyrimidines with combined LH and FSH agonistic activity. Download PDFInfo
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- ZA200401459B ZA200401459B ZA200401459A ZA200401459A ZA200401459B ZA 200401459 B ZA200401459 B ZA 200401459B ZA 200401459 A ZA200401459 A ZA 200401459A ZA 200401459 A ZA200401459 A ZA 200401459A ZA 200401459 B ZA200401459 B ZA 200401459B
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- South Africa
- Prior art keywords
- alkyl
- compound according
- composition
- substance
- thieno
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- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 1
- 230000002710 gonadal effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000960 hypophysis hormone Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
- 238000005462 in vivo assay Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 208000000509 infertility Diseases 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 231100000535 infertility Toxicity 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000029849 luteinization Effects 0.000 description 1
- 208000037106 male hypogonadism Diseases 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- 238000013160 medical therapy Methods 0.000 description 1
- 230000021121 meiosis Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 102000006240 membrane receptors Human genes 0.000 description 1
- 108020004084 membrane receptors Proteins 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000010369 molecular cloning Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- YPBZUENVVKSCOE-UHFFFAOYSA-N o-ethyl 5-amino-2-methyl-4-(3-nitrophenyl)thieno[2,3-d]pyrimidine-6-carbothioate Chemical compound C=12C(N)=C(C(=S)OCC)SC2=NC(C)=NC=1C1=CC=CC([N+]([O-])=O)=C1 YPBZUENVVKSCOE-UHFFFAOYSA-N 0.000 description 1
- DZLHEBGBSVOAON-UHFFFAOYSA-N o-ethyl 5-amino-4-(3-aminophenyl)-2-methylthieno[2,3-d]pyrimidine-6-carbothioate Chemical compound C=12C(N)=C(C(=S)OCC)SC2=NC(C)=NC=1C1=CC=CC(N)=C1 DZLHEBGBSVOAON-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 210000002394 ovarian follicle Anatomy 0.000 description 1
- 230000027758 ovulation cycle Effects 0.000 description 1
- 230000000624 ovulatory effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002281 placental hormone Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 230000023603 positive regulation of transcription initiation, DNA-dependent Effects 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 230000027272 reproductive process Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002741 site-directed mutagenesis Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000010009 steroidogenesis Effects 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000002381 testicular Effects 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
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- 238000012546 transfer Methods 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/06—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
-
- 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
- A61P5/06—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
- A61P5/08—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH for decreasing, blocking or antagonising the activity of the anterior pituitary hormones
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Reproductive Health (AREA)
- Diabetes (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01203328 | 2001-09-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200401459B true ZA200401459B (en) | 2004-11-22 |
Family
ID=8180877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200401459A ZA200401459B (en) | 2001-09-04 | 2004-02-23 | Glycine-substituted thieno[2,3-d]pyrimidines with combined LH and FSH agonistic activity. |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US7375109B2 (ja) |
| EP (1) | EP1427734B1 (ja) |
| JP (1) | JP4263094B2 (ja) |
| KR (1) | KR100891630B1 (ja) |
| CN (1) | CN1261437C (ja) |
| AR (1) | AR036408A1 (ja) |
| AT (1) | ATE309251T1 (ja) |
| AU (1) | AU2002333750B2 (ja) |
| BR (1) | BR0212173A (ja) |
| CA (1) | CA2457212C (ja) |
| CY (1) | CY1106052T1 (ja) |
| DE (1) | DE60207280T2 (ja) |
| DK (1) | DK1427734T3 (ja) |
| EC (1) | ECSP044990A (ja) |
| ES (1) | ES2252540T3 (ja) |
| HR (1) | HRP20040194A2 (ja) |
| HU (1) | HUP0401443A3 (ja) |
| IL (2) | IL160194A0 (ja) |
| IS (1) | IS2419B (ja) |
| MX (1) | MXPA04002046A (ja) |
| NO (1) | NO328792B1 (ja) |
| NZ (1) | NZ531375A (ja) |
| PE (1) | PE20030467A1 (ja) |
| PL (1) | PL368388A1 (ja) |
| RU (1) | RU2294331C2 (ja) |
| WO (1) | WO2003020727A1 (ja) |
| ZA (1) | ZA200401459B (ja) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6890923B2 (en) * | 2002-12-16 | 2005-05-10 | Astrazeneca Ab | Compounds |
| KR100666484B1 (ko) * | 2005-02-04 | 2007-01-09 | 삼성전자주식회사 | 반도체 메모리 장치의 입출력 회로 및 입출력 방법 |
| US8741259B2 (en) * | 2008-10-20 | 2014-06-03 | Marvin C. Gershengorn | Low molecular weight thyroid stimulating hormone receptor (TSHR) agonists |
| CN101762915B (zh) * | 2008-12-24 | 2013-04-17 | 北京京东方光电科技有限公司 | Tft-lcd阵列基板及其驱动方法 |
| CN102791705B (zh) | 2010-04-08 | 2016-08-03 | 美国政府(由卫生和人类服务部的部长所代表) | 用于tsh受体的反向激动剂和中性拮抗剂 |
| EP4119564A1 (en) * | 2012-09-28 | 2023-01-18 | Takeda Pharmaceutical Company Limited | Production method of thienopyrimidine derivative |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2054784T3 (es) | 1987-08-08 | 1994-08-16 | Akzo Nv | Un metodo para la fabricacion de un implante. |
| TW564247B (en) | 1999-04-08 | 2003-12-01 | Akzo Nobel Nv | Bicyclic heteraromatic compound |
-
2002
- 2002-08-29 AT AT02797646T patent/ATE309251T1/de not_active IP Right Cessation
- 2002-08-29 IL IL16019402A patent/IL160194A0/xx unknown
- 2002-08-29 CA CA2457212A patent/CA2457212C/en not_active Expired - Fee Related
- 2002-08-29 CN CNB02817240XA patent/CN1261437C/zh not_active Expired - Fee Related
- 2002-08-29 JP JP2003524997A patent/JP4263094B2/ja not_active Expired - Fee Related
- 2002-08-29 US US10/488,483 patent/US7375109B2/en not_active Expired - Lifetime
- 2002-08-29 MX MXPA04002046A patent/MXPA04002046A/es active IP Right Grant
- 2002-08-29 WO PCT/EP2002/009648 patent/WO2003020727A1/en active IP Right Grant
- 2002-08-29 HU HU0401443A patent/HUP0401443A3/hu unknown
- 2002-08-29 DK DK02797646T patent/DK1427734T3/da active
- 2002-08-29 ES ES02797646T patent/ES2252540T3/es not_active Expired - Lifetime
- 2002-08-29 NZ NZ531375A patent/NZ531375A/en not_active IP Right Cessation
- 2002-08-29 RU RU2004110036/04A patent/RU2294331C2/ru not_active IP Right Cessation
- 2002-08-29 EP EP02797646A patent/EP1427734B1/en not_active Expired - Lifetime
- 2002-08-29 PL PL02368388A patent/PL368388A1/xx not_active Application Discontinuation
- 2002-08-29 DE DE60207280T patent/DE60207280T2/de not_active Expired - Lifetime
- 2002-08-29 KR KR1020047003096A patent/KR100891630B1/ko not_active IP Right Cessation
- 2002-08-29 AU AU2002333750A patent/AU2002333750B2/en not_active Ceased
- 2002-08-29 BR BR0212173-5A patent/BR0212173A/pt not_active IP Right Cessation
- 2002-09-02 AR ARP020103310A patent/AR036408A1/es unknown
- 2002-09-03 PE PE2002000839A patent/PE20030467A1/es not_active Application Discontinuation
-
2004
- 2004-02-03 IL IL160194A patent/IL160194A/en not_active IP Right Cessation
- 2004-02-13 IS IS7152A patent/IS2419B/is unknown
- 2004-02-23 ZA ZA200401459A patent/ZA200401459B/en unknown
- 2004-02-26 EC EC2004004990A patent/ECSP044990A/es unknown
- 2004-02-26 HR HR20040194A patent/HRP20040194A2/hr not_active Application Discontinuation
- 2004-03-03 NO NO20040922A patent/NO328792B1/no not_active IP Right Cessation
-
2005
- 2005-12-22 CY CY20051101587T patent/CY1106052T1/el unknown
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