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 PDF

Info

Publication number: ZA200401459B
Authority: ZA; South Africa
Prior art keywords: alkyl; compound according; composition; substance; thieno
Prior art date: 2001-09-04

Application number

ZA200401459A

Other languages

English (en)

Inventor

Robert Gerard Jules Ma Hanssen

Jan Kelder

Cornelis Marius Timmers

Original Assignee

Akzo Nobel Nv

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2001-09-04

Filing date

2004-02-23

Publication date

2004-11-22

2004-02-23 Application filed by Akzo Nobel Nv filed Critical Akzo Nobel Nv

2004-11-22 Publication of ZA200401459B publication Critical patent/ZA200401459B/en

Links

-1 Glycine-substituted thieno[2,3-d]pyrimidines Chemical class 0.000 title claims description 15
230000001270 agonistic effect Effects 0.000 title description 12
150000001875 compounds Chemical class 0.000 claims description 59
239000000203 mixture Substances 0.000 claims description 32
125000000217 alkyl group Chemical group 0.000 claims description 27
238000000034 method Methods 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
230000035558 fertility Effects 0.000 claims description 6
DDWBRNXDKNIQDY-UHFFFAOYSA-N thieno[2,3-d]pyrimidine Chemical class N1=CN=C2SC=CC2=C1 DDWBRNXDKNIQDY-UHFFFAOYSA-N 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000001072 heteroaryl group Chemical group 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000003282 alkyl amino group Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
208000021267 infertility disease Diseases 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
238000002560 therapeutic procedure Methods 0.000 claims description 2
239000000126 substance Substances 0.000 claims 8
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108010073521 Luteinizing Hormone Proteins 0.000 description 28
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JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 19
210000004027 cell Anatomy 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
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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
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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
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239000007788 liquid Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
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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
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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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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)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Endocrinology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Diabetes (AREA)
Reproductive Health (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)

ZA200401459A 2001-09-04 2004-02-23 Glycine-substituted thieno[2,3-d]pyrimidines with combined LH and FSH agonistic activity. ZA200401459B (en)

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 (de)
EP (1)	EP1427734B1 (de)
JP (1)	JP4263094B2 (de)
KR (1)	KR100891630B1 (de)
CN (1)	CN1261437C (de)
AR (1)	AR036408A1 (de)
AT (1)	ATE309251T1 (de)
AU (1)	AU2002333750B2 (de)
BR (1)	BR0212173A (de)
CA (1)	CA2457212C (de)
CY (1)	CY1106052T1 (de)
DE (1)	DE60207280T2 (de)
DK (1)	DK1427734T3 (de)
EC (1)	ECSP044990A (de)
ES (1)	ES2252540T3 (de)
HR (1)	HRP20040194A2 (de)
HU (1)	HUP0401443A3 (de)
IL (2)	IL160194A0 (de)
IS (1)	IS2419B (de)
MX (1)	MXPA04002046A (de)
NO (1)	NO328792B1 (de)
NZ (1)	NZ531375A (de)
PE (1)	PE20030467A1 (de)
PL (1)	PL368388A1 (de)
RU (1)	RU2294331C2 (de)
WO (1)	WO2003020727A1 (de)
ZA (1)	ZA200401459B (de)

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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
EP2563777A4 (de)	2010-04-08	2013-09-04	Us Health	Inverse agonisten und neutrale agonisten für den tsh-rezeptor
PT3415517T (pt)	2012-09-28	2022-05-13	Takeda Pharmaceuticals Co	Forma cristalina de 1-(4-1-(2,6-difluorobenzil)-5- dimetilaminometil-3-(6-metoxipiridazin-3-il)-2,4-dioxo- 1,2,3,4-tetrahidrotieno(2,3-d)-pirimidin-6-il)fenil)-3- metoxiureia
CN115279769A (zh)	2019-10-10	2022-11-01	梦欧文科学有限责任公司	N-(4-(1-(2,6-二氟苄基)-5-((二甲基氨基)甲基)-3-(6-甲氧基-3-哒嗪基)-2,4-二氧代-1,2,3,4-四氢噻吩并[2,3-d]嘧啶-6-基)苯基)-n’-甲氧基脲的结晶形式

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* Cited by examiner, † Cited by third party
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.
DE19632423A1 (de) *	1996-08-12	1998-02-19	Merck Patent Gmbh	Thienopyrimidine
TW564247B (en)	1999-04-08	2003-12-01	Akzo Nobel Nv	Bicyclic heteraromatic compound

2002
- 2002-08-29 NZ NZ531375A patent/NZ531375A/en not_active IP Right Cessation
- 2002-08-29 WO PCT/EP2002/009648 patent/WO2003020727A1/en not_active Ceased
- 2002-08-29 KR KR1020047003096A patent/KR100891630B1/ko not_active Expired - Fee Related
- 2002-08-29 HR HR20040194A patent/HRP20040194A2/hr not_active Application Discontinuation
- 2002-08-29 DK DK02797646T patent/DK1427734T3/da active
- 2002-08-29 DE DE60207280T patent/DE60207280T2/de not_active Expired - Lifetime
- 2002-08-29 BR BR0212173-5A patent/BR0212173A/pt not_active IP Right Cessation
- 2002-08-29 CA CA2457212A patent/CA2457212C/en not_active Expired - Fee Related
- 2002-08-29 AT AT02797646T patent/ATE309251T1/de not_active IP Right Cessation
- 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 IL IL16019402A patent/IL160194A0/xx unknown
- 2002-08-29 AU AU2002333750A patent/AU2002333750B2/en not_active Ceased
- 2002-08-29 PL PL02368388A patent/PL368388A1/xx not_active Application Discontinuation
- 2002-08-29 ES ES02797646T patent/ES2252540T3/es not_active Expired - Lifetime
- 2002-08-29 MX MXPA04002046A patent/MXPA04002046A/es active IP Right Grant
- 2002-08-29 RU RU2004110036/04A patent/RU2294331C2/ru not_active IP Right Cessation
- 2002-08-29 HU HU0401443A patent/HUP0401443A3/hu unknown
- 2002-08-29 EP EP02797646A patent/EP1427734B1/de not_active Expired - Lifetime
- 2002-08-29 CN CNB02817240XA patent/CN1261437C/zh not_active Expired - Fee Related
- 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
- 2004-03-03 NO NO20040922A patent/NO328792B1/no not_active IP Right Cessation
2005
- 2005-12-22 CY CY20051101587T patent/CY1106052T1/el unknown

Also Published As

Publication number	Publication date
ATE309251T1 (de)	2005-11-15
CN1261437C (zh)	2006-06-28
AR036408A1 (es)	2004-09-08
CA2457212C (en)	2011-02-15
PE20030467A1 (es)	2003-05-26
DE60207280T2 (de)	2006-05-18
RU2004110036A (ru)	2005-10-10
EP1427734B1 (de)	2005-11-09
EP1427734A1 (de)	2004-06-16
CY1106052T1 (el)	2011-04-06
NO328792B1 (no)	2010-05-18
IL160194A0 (en)	2004-07-25
IL160194A (en)	2009-06-15
DE60207280D1 (de)	2005-12-15
AU2002333750B2 (en)	2008-02-21
ES2252540T3 (es)	2006-05-16
CA2457212A1 (en)	2003-03-13
US7375109B2 (en)	2008-05-20
JP2005504784A (ja)	2005-02-17
DK1427734T3 (da)	2006-03-06
RU2294331C2 (ru)	2007-02-27
PL368388A1 (en)	2005-03-21
KR20040029135A (ko)	2004-04-03
IS7152A (is)	2004-02-13
ECSP044990A (es)	2004-04-28
HUP0401443A3 (en)	2008-05-28
US20040180907A1 (en)	2004-09-16
MXPA04002046A (es)	2004-07-16
JP4263094B2 (ja)	2009-05-13
IS2419B (is)	2008-10-15
HRP20040194A2 (en)	2004-08-31
NO20040922L (no)	2004-03-03
BR0212173A (pt)	2004-07-20
HUP0401443A2 (hu)	2004-11-29
NZ531375A (en)	2005-06-24
KR100891630B1 (ko)	2009-04-03
WO2003020727A1 (en)	2003-03-13
CN1551883A (zh)	2004-12-01

Publication	Publication Date	Title
US6569863B1 (en)	2003-05-27	Bicyclic heteroamatic compounds useful as LH agonists
AU2002337035B2 (en)	2008-04-24	Thieno[2,3-d]pyrimidines with combined LH and FSH agonistic activity
US20070197527A1 (en)	2007-08-23	Bicyclic heteroaromatic compounds
EP3080126B1 (de)	2019-08-28	Purinderivate als modulatoren der tnf-aktivität
AU2002337035A1 (en)	2003-06-05	Thieno[2,3-d]pyrimidines with combined LH and FSH agonistic activity
EP1427734B1 (de)	2005-11-09	GLYCINSUBSTITUIERTE THIENO[2,3-d]PYRIMIDINE MIT KOMBINIERTER LH- UND FSH-AGONISTISCHER WIRKUNG
AU2002333750A1 (en)	2003-06-05	Glycine-substituted thieno[2,3-d]pyrimidines with combined LH and FSH agonistic activity
HK1054942B (en)	2008-04-03	Bicyclic heteroaromatic compounds