HRP20040194A2 - 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
- Publication number
- HRP20040194A2 HRP20040194A2 HR20040194A HRP20040194A HRP20040194A2 HR P20040194 A2 HRP20040194 A2 HR P20040194A2 HR 20040194 A HR20040194 A HR 20040194A HR P20040194 A HRP20040194 A HR P20040194A HR P20040194 A2 HRP20040194 A2 HR P20040194A2
- Authority
- HR
- Croatia
- Prior art keywords
- amino
- pyrimidine
- thieno
- mixture
- phenyl
- Prior art date
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- 230000001270 agonistic effect Effects 0.000 title description 11
- 150000003230 pyrimidines Chemical class 0.000 title 1
- 239000000203 mixture Substances 0.000 claims description 120
- 150000001875 compounds Chemical class 0.000 claims description 84
- -1 cyano, amino Chemical group 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- DDWBRNXDKNIQDY-UHFFFAOYSA-N thieno[2,3-d]pyrimidine Chemical class N1=CN=C2SC=CC2=C1 DDWBRNXDKNIQDY-UHFFFAOYSA-N 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
- 230000035558 fertility Effects 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 2
- 208000021267 infertility disease Diseases 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
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- 239000012453 solvate Substances 0.000 claims 1
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 80
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 68
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 67
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 63
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 60
- 239000000243 solution Substances 0.000 description 56
- 238000004128 high performance liquid chromatography Methods 0.000 description 53
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- 239000012043 crude product Substances 0.000 description 17
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- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
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- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
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- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
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- 229910019213 POCl3 Inorganic materials 0.000 description 6
- 239000012317 TBTU Substances 0.000 description 6
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 6
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
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- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 5
- FDMHRMOZWKVAEJ-UHFFFAOYSA-N 5-amino-4-[3-[(2-bromoacetyl)amino]phenyl]-n-tert-butyl-2-thiophen-2-ylthieno[2,3-d]pyrimidine-6-carboxamide Chemical compound C=12C(N)=C(C(=O)NC(C)(C)C)SC2=NC(C=2SC=CC=2)=NC=1C1=CC=CC(NC(=O)CBr)=C1 FDMHRMOZWKVAEJ-UHFFFAOYSA-N 0.000 description 5
- XSVLGHKETAQFBO-UHFFFAOYSA-N 5-amino-n-tert-butyl-4-[3-[[2-[ethyl(2-methoxyethyl)amino]acetyl]amino]phenyl]-2-methylsulfinylthieno[2,3-d]pyrimidine-6-carboxamide Chemical compound COCCN(CC)CC(=O)NC1=CC=CC(C=2C=3C(N)=C(C(=O)NC(C)(C)C)SC=3N=C(N=2)S(C)=O)=C1 XSVLGHKETAQFBO-UHFFFAOYSA-N 0.000 description 5
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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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01203328 | 2001-09-04 | ||
| PCT/EP2002/009648 WO2003020727A1 (en) | 2001-09-04 | 2002-08-29 | GLYCINE-SUBSTITUTED THIENO [2,3-d]PYRIMIDINES WITH COMBINED LH AND FSH AGONISTIC ACTIVITY |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20040194A2 true HRP20040194A2 (en) | 2004-08-31 |
Family
ID=8180877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20040194A HRP20040194A2 (en) | 2001-09-04 | 2004-02-26 | GLYCINE-SUBSTITUTED THIENO [2,3-d] PYRIMIDINES WITH COMBINED LH AND FSH AGONISTIC ACTIVITY |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US7375109B2 (ko) |
| EP (1) | EP1427734B1 (ko) |
| JP (1) | JP4263094B2 (ko) |
| KR (1) | KR100891630B1 (ko) |
| CN (1) | CN1261437C (ko) |
| AR (1) | AR036408A1 (ko) |
| AT (1) | ATE309251T1 (ko) |
| AU (1) | AU2002333750B2 (ko) |
| BR (1) | BR0212173A (ko) |
| CA (1) | CA2457212C (ko) |
| CY (1) | CY1106052T1 (ko) |
| DE (1) | DE60207280T2 (ko) |
| DK (1) | DK1427734T3 (ko) |
| EC (1) | ECSP044990A (ko) |
| ES (1) | ES2252540T3 (ko) |
| HR (1) | HRP20040194A2 (ko) |
| HU (1) | HUP0401443A3 (ko) |
| IL (2) | IL160194A0 (ko) |
| IS (1) | IS2419B (ko) |
| MX (1) | MXPA04002046A (ko) |
| NO (1) | NO328792B1 (ko) |
| NZ (1) | NZ531375A (ko) |
| PE (1) | PE20030467A1 (ko) |
| PL (1) | PL368388A1 (ko) |
| RU (1) | RU2294331C2 (ko) |
| WO (1) | WO2003020727A1 (ko) |
| ZA (1) | ZA200401459B (ko) |
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 |
| CA2741030A1 (en) | 2008-10-20 | 2010-04-29 | 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 |
| CA2789818A1 (en) | 2010-04-08 | 2011-10-13 | The United States Of America, As Represented By The Secretary, Departmen T Of Health And Human Services | Inverse agonists and neutral antagonists for the tsh receptor |
| PL2900675T3 (pl) * | 2012-09-28 | 2019-08-30 | Takeda Pharmaceutical Company Limited | Sposób wytwarzania pochodnej tienopirymidyny |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE86484T1 (de) | 1987-08-08 | 1993-03-15 | Akzo Nv | Kontrazeptives implantat. |
| TW564247B (en) | 1999-04-08 | 2003-12-01 | Akzo Nobel Nv | Bicyclic heteraromatic compound |
-
2002
- 2002-08-29 PL PL02368388A patent/PL368388A1/xx not_active Application Discontinuation
- 2002-08-29 BR BR0212173-5A patent/BR0212173A/pt not_active IP Right Cessation
- 2002-08-29 DE DE60207280T patent/DE60207280T2/de not_active Expired - Lifetime
- 2002-08-29 US US10/488,483 patent/US7375109B2/en not_active Expired - Lifetime
- 2002-08-29 DK DK02797646T patent/DK1427734T3/da active
- 2002-08-29 JP JP2003524997A patent/JP4263094B2/ja not_active Expired - Fee Related
- 2002-08-29 HU HU0401443A patent/HUP0401443A3/hu unknown
- 2002-08-29 KR KR1020047003096A patent/KR100891630B1/ko 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 IL IL16019402A patent/IL160194A0/xx unknown
- 2002-08-29 WO PCT/EP2002/009648 patent/WO2003020727A1/en active IP Right Grant
- 2002-08-29 CA CA2457212A patent/CA2457212C/en not_active Expired - Fee Related
- 2002-08-29 NZ NZ531375A patent/NZ531375A/en not_active IP Right Cessation
- 2002-08-29 CN CNB02817240XA patent/CN1261437C/zh not_active Expired - Fee Related
- 2002-08-29 ES ES02797646T patent/ES2252540T3/es not_active Expired - Lifetime
- 2002-08-29 AU AU2002333750A patent/AU2002333750B2/en not_active Ceased
- 2002-08-29 AT AT02797646T patent/ATE309251T1/de not_active IP Right Cessation
- 2002-08-29 MX MXPA04002046A patent/MXPA04002046A/es active IP Right Grant
- 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 HR HR20040194A patent/HRP20040194A2/hr not_active Application Discontinuation
- 2004-02-26 EC EC2004004990A patent/ECSP044990A/es unknown
- 2004-03-03 NO NO20040922A patent/NO328792B1/no not_active IP Right Cessation
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2005
- 2005-12-22 CY CY20051101587T patent/CY1106052T1/el unknown
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