OA11920A - Thienopyrimidine compounds, their production and use. - Google Patents

Thienopyrimidine compounds, their production and use. Download PDF

Info

Publication number: OA11920A
Authority: OA; OAPI
Prior art keywords: compound; group; sait; hydrogen atom; alkyl group
Prior art date: 1999-03-24

Application number

OA1200100243A

Other languages

English (en)

Inventor

Nobuo Choh

Shuichi Furuya

Yoshi Nara

Nobuhiro Suzuki

Original Assignee

Takeda Chemical Industries Ltd

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.)

1999-03-24

Filing date

2000-03-23

Publication date

2006-04-12

2000-03-23 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

2006-04-12 Publication of OA11920A publication Critical patent/OA11920A/en

Links

238000004519 manufacturing process Methods 0.000 title claims description 11
RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical class C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 225
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 19
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 10
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 8
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 8
125000005530 alkylenedioxy group Chemical group 0.000 claims abstract description 6
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims description 46
239000000203 mixture Substances 0.000 claims description 44
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
125000003545 alkoxy group Chemical group 0.000 claims description 25
229940088597 hormone Drugs 0.000 claims description 11
239000005556 hormone Substances 0.000 claims description 11
125000005843 halogen group Chemical group 0.000 claims description 8
239000000546 pharmaceutical excipient Substances 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 7
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 2
239000003488 releasing hormone Substances 0.000 claims 1
150000003839 salts Chemical class 0.000 abstract description 9
230000000694 effects Effects 0.000 abstract description 8
201000010099 disease Diseases 0.000 abstract description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 6
239000003163 gonadal steroid hormone Substances 0.000 abstract description 3
229910052736 halogen Inorganic materials 0.000 abstract description 3
150000002367 halogens Chemical class 0.000 abstract description 3
229910052739 hydrogen Inorganic materials 0.000 abstract 4
239000001257 hydrogen Substances 0.000 abstract 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
150000002431 hydrogen Chemical class 0.000 abstract 2
230000001419 dependent effect Effects 0.000 abstract 1
239000000243 solution Substances 0.000 description 88
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 58
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 50
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 49
239000002904 solvent Substances 0.000 description 43
-1 methoxy, ethoxy, propoxy, butoxy, isopropoxy, t-butoxy Chemical group 0.000 description 36
230000002829 reductive effect Effects 0.000 description 35
235000002639 sodium chloride Nutrition 0.000 description 35
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
239000011541 reaction mixture Substances 0.000 description 33
238000006243 chemical reaction Methods 0.000 description 32
238000001816 cooling Methods 0.000 description 27
239000011780 sodium chloride Substances 0.000 description 27
229960002668 sodium chloride Drugs 0.000 description 27
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
229960001701 chloroform Drugs 0.000 description 25
239000000579 Gonadotropin-Releasing Hormone Substances 0.000 description 24
238000005160 1H NMR spectroscopy Methods 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
101000857870 Squalus acanthias Gonadoliberin Proteins 0.000 description 21
XLXSAKCOAKORKW-AQJXLSMYSA-N gonadorelin Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)NCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 XLXSAKCOAKORKW-AQJXLSMYSA-N 0.000 description 21
229940035638 gonadotropin-releasing hormone Drugs 0.000 description 21
239000000741 silica gel Substances 0.000 description 20
229910002027 silica gel Inorganic materials 0.000 description 20
229960001866 silicon dioxide Drugs 0.000 description 20
238000000034 method Methods 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
239000000284 extract Substances 0.000 description 18
238000000921 elemental analysis Methods 0.000 description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 17
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 15
230000003042 antagnostic effect Effects 0.000 description 15
239000003814 drug Substances 0.000 description 15
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
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FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 12
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 12
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 12
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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239000002585 base Substances 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
239000003102 growth factor Substances 0.000 description 9
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
102000005962 receptors Human genes 0.000 description 9
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229920006395 saturated elastomer Polymers 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
210000004027 cell Anatomy 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 8
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BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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JGOOQALRLGHKIY-UHFFFAOYSA-N 1h-thieno[2,3-d]pyrimidine-2,4-dione Chemical compound O=C1NC(=O)NC2=C1C=CS2 JGOOQALRLGHKIY-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
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241001465754 Metazoa Species 0.000 description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
241000700159 Rattus Species 0.000 description 7
229920002472 Starch Polymers 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
239000003112 inhibitor Substances 0.000 description 7
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LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
239000006216 vaginal suppository Substances 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- 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
- 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
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- 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
- 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
- A61P5/02—Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin
- A61P5/04—Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin for decreasing, blocking or antagonising the activity of the hypothalamic hormones
- 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
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Endocrinology (AREA)
Engineering & Computer Science (AREA)
Reproductive Health (AREA)
Diabetes (AREA)
Gynecology & Obstetrics (AREA)
Pregnancy & Childbirth (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

OA1200100243A 1999-03-24 2000-03-23 Thienopyrimidine compounds, their production and use. OA11920A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP7937199		1999-03-24
JP2000018019		2000-01-25

Publications (1)

Publication Number	Publication Date
OA11920A true OA11920A (en)	2006-04-12

Family

ID=26420391

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200100243A OA11920A (en)	1999-03-24	2000-03-23	Thienopyrimidine compounds, their production and use.

Country Status (28)

Country	Link
US (1)	US6340686B1 (de)
EP (1)	EP1163244B1 (de)
JP (1)	JP3240293B2 (de)
KR (2)	KR100533483B1 (de)
CN (1)	CN1349536A (de)
AR (1)	AR023152A1 (de)
AT (1)	ATE261449T1 (de)
AU (1)	AU764019B2 (de)
BR (1)	BR0009297A (de)
CA (1)	CA2368108C (de)
CZ (1)	CZ294747B6 (de)
DE (1)	DE60008862T2 (de)
DK (1)	DK1163244T3 (de)
ES (1)	ES2212992T3 (de)
HK (1)	HK1042495B (de)
HU (1)	HUP0200550A3 (de)
ID (1)	ID30393A (de)
IL (1)	IL145549A (de)
MX (1)	MXPA01009566A (de)
MY (1)	MY124726A (de)
NO (1)	NO20014603L (de)
NZ (1)	NZ514737A (de)
OA (1)	OA11920A (de)
PL (1)	PL351202A1 (de)
PT (1)	PT1163244E (de)
SK (1)	SK13552001A3 (de)
TW (1)	TWI225863B (de)
WO (1)	WO2000056739A1 (de)

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6828415B2 (en) *	1993-02-19	2004-12-07	Zentaris Gmbh	Oligopeptide lyophilisate, their preparation and use
KR20030005205A (ko) *	2000-02-29	2003-01-17	다케다 야쿠힌 고교 가부시키가이샤	티에노피리미딘 유도체의 제조 방법
US20030134863A1 (en) *	2000-04-13	2003-07-17	Shuichi Furuya	Preventives/remedies for alzheimer's disease
EP1291023A1 (de) *	2000-06-14	2003-03-12	Takeda Chemical Industries, Ltd.	Formulierungen mit verzögerter wirkstofffreisetzung
AU2001288102A1 (en) *	2000-09-22	2002-04-02	Takeda Chemical Industries Ltd.	Solid preparations
WO2002043766A1 (en) *	2000-11-29	2002-06-06	Takeda Chemical Industries, Ltd.	Medicinal compositions and process for producing the same
AU2002221139A1 (en) *	2000-12-15	2002-06-24	Takeda Chemical Industries Ltd.	Medicinal compositions of nonpeptidyl gonadotropin-releasing hormone agonist or antagonist, process for producing the same and use thereof
WO2002078669A1 (fr) *	2001-03-30	2002-10-10	Takeda Chemical Industries, Ltd.	Solutions medicinales
JP2005500352A (ja)	2001-08-02	2005-01-06	ニューロクラインバイオサイエンシーズ，インコーポレイテッド	ゴナドトロピン放出ホルモンレセプター（ＧｎＲＨ）アンタゴニストとしての１，２，４−トリアジン−３，５−ジオン
EP1411941A2 (de)	2001-08-02	2004-04-28	Neurocrine Biosciences, Inc.	Pyridinon- und pyridazinonderivate als antagonisten des gonadotropin-freisetzungshormon-rezeptors
US6939883B2 (en)	2001-08-02	2005-09-06	Neurocrine Biosciences, Inc.	Gonadotropin-releasing hormone receptor antagonists and methods relating thereto
AU2002324586B2 (en)	2001-08-02	2008-04-24	Neurocrine Biosciences, Inc.	1,3,5-triazine-2,4,6-triones, preparation and use as gonadotropin-releasing hormone receptor antagonists
WO2003011870A1 (en) *	2001-08-02	2003-02-13	Neurocrine Biosciences, Inc.	Gonadotropin-releasing hormone receptor antagonists
US7569570B2 (en) *	2002-01-30	2009-08-04	Takeda Pharmaceutical Company Limited	Thienopyrimidines, process for preparing the same and use thereof
EP1495768A4 (de)	2002-04-12	2007-12-05	Takeda Pharmaceutical	Mittel zur prävention/behandlung von hitzewallungen
JP2006508050A (ja) *	2002-08-21	2006-03-09	アストラゼネカアクチボラグ	ゴナドトロピン放出ホルモンのアンタゴニストとしてのチエノピロール化合物
EP1591446B1 (de)	2003-01-29	2013-03-06	Takeda Pharmaceutical Company Limited	Thienopyrimidinverbindungen und deren Verwendung
GB0307777D0 (en)	2003-04-04	2003-05-07	Medical Res Council	Conjugate compounds
US20060083017A1 (en) *	2004-10-18	2006-04-20	Bwt Propety, Inc.	Solid-state lighting apparatus for navigational aids
KR20080041662A (ko)	2005-07-22	2008-05-13	다케다 야쿠힌 고교 가부시키가이샤	조기 배란 예방제
EP2329823A4 (de)	2008-09-03	2013-04-03	Takeda Pharmaceutical	Verfahren zur erhöhung der absorptionsfähigkeit eines präparats sowie präparat mit erhöhter absorptionsfähigkeit
MX357841B (es) *	2012-02-28	2018-07-26	Tiumbio Co Ltd	Antagonistas de los receptores de la hormona liberadora de gonadotropina, método para la preparación de éstos y composición farmacéutica que los contienen.
PL2900675T3 (pl)	2012-09-28	2019-08-30	Takeda Pharmaceutical Company Limited	Sposób wytwarzania pochodnej tienopirymidyny
CA2978223A1 (en) *	2015-02-26	2016-09-01	Takeda Pharmaceutical Company Limited	Formulations of n-(4-(1-(2,6-difluorobenzyl)-5-((dimethyl amino)methyl)-3-(6-methoxy-3-pyridazinyl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl)phenyl)-n'-methoxyurea
EP3518933B2 (de)	2016-09-30	2025-02-26	Sumitomo Pharma Switzerland GmbH	Verfahren zur behandlung von gebärmuttermyomen und endometriose
CN110248661A (zh)	2016-09-30	2019-09-17	梦欧文科学有限责任公司	前列腺癌的治疗
KR101973074B1 (ko)	2018-11-30	2019-04-26	주식회사 티움바이오	퓨로피리미딘 화합물의 염 및 결정형, 및 이를 포함하는 약학적 조성물
CN111943960B (zh) *	2019-07-29	2022-02-15	广东东阳光药业有限公司	取代的嘧啶二酮类化合物及其用途
JP2022551316A (ja)	2019-10-10	2022-12-08	ミオバントサイエンシズゲーエムベーハー	Ｎ－（４－（１－（２，６－ジフルオロベンジル）－５－（（ジメチルアミノ）メチル）－３－（６－メトキシ－３－ピリダジニル）－２，４－ジオキソ－１，２，３，４－テトラヒドロチエノ［２，３－ｄ］ピリミジン－６－イル）フェニル）－Ｎ’－メトキシ尿素の結晶形
CN111574534B (zh) *	2020-05-25	2021-06-04	东莞市东阳光新药研发有限公司	苯基取代的噻吩并[2,3-d]嘧啶-2,4(1H,3H)-二酮类化合物及其用途
BR112022023937A2 (pt)	2020-05-29	2022-12-27	Myovant Sciences Gmbh	Formas de dosagem oral sólidas de combinação de antagonistas do hormônio liberador de gonadotropina
CN111925379B (zh) *	2020-07-31	2022-02-15	广东东阳光药业有限公司	含氮杂芳基取代的嘧啶二酮类化合物及其用途
CN111909168B (zh) *	2020-07-31	2022-02-01	广东东阳光药业有限公司	含氮杂环基取代的嘧啶二酮类化合物及其用途
CN112047957B (zh) *	2020-09-09	2022-02-01	广东东阳光药业有限公司	取代的嘧啶二酮类化合物及其用途
CN113754679B (zh) *	2020-09-09	2023-04-07	广东东阳光药业有限公司	取代的嘧啶二酮类化合物及其用途
CN113563303B (zh) *	2020-12-30	2022-04-12	上海博志研新药物技术有限公司	瑞卢戈利中间体及其制备方法
CN115260211B (zh) *	2021-04-29	2024-02-06	长春金赛药业有限责任公司	含噻吩稠环类衍生物、药物组合物及其制备方法和应用
CN113717149A (zh) *	2021-09-29	2021-11-30	成都伊诺达博医药科技有限公司	一种瑞卢戈利关键中间体及其制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TW449600B (en) *	1994-04-19	2001-08-11	Takeda Chemical Industries Ltd	Condensed-ring thiophene derivatives, their production and use
UY23948A1 (es) *	1995-02-08	2001-10-25	Takeda Chemical Industries Ltd	Derivados de anillos condensados de tiofeno su producción y uso.
US5627786A (en) *	1995-02-10	1997-05-06	Micron Quantum Devices, Inc.	Parallel processing redundancy scheme for faster access times and lower die area
WO1996028405A1 (fr) *	1995-03-10	1996-09-19	Nitto Chemical Industry Co., Ltd.	Procede de production de derives de 1,2-ethanediol

2000
- 2000-03-08 TW TW089104127A patent/TWI225863B/zh not_active IP Right Cessation
- 2000-03-21 MY MYPI20001112 patent/MY124726A/en unknown
- 2000-03-23 CA CA002368108A patent/CA2368108C/en not_active Expired - Fee Related
- 2000-03-23 MX MXPA01009566A patent/MXPA01009566A/es active IP Right Grant
- 2000-03-23 JP JP2000087051A patent/JP3240293B2/ja not_active Expired - Fee Related
- 2000-03-23 PL PL00351202A patent/PL351202A1/xx not_active Application Discontinuation
- 2000-03-23 NZ NZ514737A patent/NZ514737A/en unknown
- 2000-03-23 SK SK1355-2001A patent/SK13552001A3/sk unknown
- 2000-03-23 KR KR10-2000-7011511A patent/KR100533483B1/ko not_active Expired - Fee Related
- 2000-03-23 DE DE60008862T patent/DE60008862T2/de not_active Expired - Lifetime
- 2000-03-23 WO PCT/JP2000/001777 patent/WO2000056739A1/en not_active Ceased
- 2000-03-23 KR KR10-2000-7011508A patent/KR100370981B1/ko not_active Expired - Fee Related
- 2000-03-23 OA OA1200100243A patent/OA11920A/en unknown
- 2000-03-23 CZ CZ20013419A patent/CZ294747B6/cs not_active IP Right Cessation
- 2000-03-23 PT PT00911308T patent/PT1163244E/pt unknown
- 2000-03-23 HK HK02104325.6A patent/HK1042495B/en not_active IP Right Cessation
- 2000-03-23 ID IDW00200102298A patent/ID30393A/id unknown
- 2000-03-23 EP EP00911308A patent/EP1163244B1/de not_active Expired - Lifetime
- 2000-03-23 BR BR0009297-5A patent/BR0009297A/pt not_active IP Right Cessation
- 2000-03-23 AU AU33262/00A patent/AU764019B2/en not_active Ceased
- 2000-03-23 IL IL14554900A patent/IL145549A/xx not_active IP Right Cessation
- 2000-03-23 CN CN00807210A patent/CN1349536A/zh active Pending
- 2000-03-23 DK DK00911308T patent/DK1163244T3/da active
- 2000-03-23 AT AT00911308T patent/ATE261449T1/de not_active IP Right Cessation
- 2000-03-23 HU HU0200550A patent/HUP0200550A3/hu unknown
- 2000-03-23 ES ES00911308T patent/ES2212992T3/es not_active Expired - Lifetime
- 2000-03-24 AR ARP000101320A patent/AR023152A1/es not_active Application Discontinuation
- 2000-05-16 US US09/571,215 patent/US6340686B1/en not_active Expired - Lifetime
2001
- 2001-09-21 NO NO20014603A patent/NO20014603L/no unknown

Also Published As

Publication number	Publication date
HUP0200550A3 (en)	2004-07-28
ES2212992T3 (es)	2004-08-16
JP3240293B2 (ja)	2001-12-17
KR20010090430A (ko)	2001-10-18
NO20014603D0 (no)	2001-09-21
DK1163244T3 (da)	2004-07-12
CA2368108C (en)	2009-12-22
CN1349536A (zh)	2002-05-15
PT1163244E (pt)	2004-07-30
ID30393A (id)	2001-11-29
EP1163244A1 (de)	2001-12-19
SK13552001A3 (sk)	2002-03-05
KR100370981B1 (ko)	2003-02-06
AU764019B2 (en)	2003-08-07
CA2368108A1 (en)	2000-09-28
IL145549A (en)	2005-11-20
HUP0200550A2 (en)	2002-06-29
WO2000056739A1 (en)	2000-09-28
HK1042495A1 (en)	2002-08-16
CZ294747B6 (cs)	2005-03-16
TWI225863B (en)	2005-01-01
AU3326200A (en)	2000-10-09
NZ514737A (en)	2003-10-31
AR023152A1 (es)	2002-09-04
ATE261449T1 (de)	2004-03-15
NO20014603L (no)	2001-11-26
HK1042495B (en)	2004-10-08
IL145549A0 (en)	2002-06-30
JP2001278884A (ja)	2001-10-10
MXPA01009566A (es)	2002-05-14
US6340686B1 (en)	2002-01-22
KR20010015920A (ko)	2001-02-26
KR100533483B1 (ko)	2005-12-05
DE60008862D1 (de)	2004-04-15
PL351202A1 (en)	2003-03-24
BR0009297A (pt)	2001-12-18
EP1163244B1 (de)	2004-03-10
MY124726A (en)	2006-06-30
DE60008862T2 (de)	2005-01-27
CZ20013419A3 (cs)	2002-02-13

Publication	Publication Date	Title
OA11920A (en)	2006-04-12	Thienopyrimidine compounds, their production and use.
RU2229299C2 (ru)	2004-05-27	Применение диазепинов для приготовления лекарственных средств, предназначенных для лечения патологических состояний или заболеваний, связанных с действием одного из рецепторов соматостатина
US6297379B1 (en)	2001-10-02	Thienopyrimidine compounds, their production and use
PL214756B1 (pl)	2013-09-30	Zwiazki tienopirymidynowe, kompozycja farmaceutyczna zawierajaca te zwiazki oraz ich zastosowanie
CZ20013605A3 (cs)	2002-03-13	Bicyklické heteroaromatické sloučeniny
JPH09169768A (ja)	1997-06-30	チエノピリミジン誘導体、その製造法および用途
US6262267B1 (en)	2001-07-17	Thienopyridine compound
US6329388B2 (en)	2001-12-11	Thienopyridine compounds, their production and use
US6297255B1 (en)	2001-10-02	Thienopyridine compounds, their production and use
JP2001278885A (ja)	2001-10-10	チエノピリミジン化合物、その製造法および用途
JP2002030087A (ja)	2002-01-29	チエノピリジン−５−カルボン酸エステル化合物、その製造法および用途
JP2003183284A (ja)	2003-07-03	含窒素複素環化合物およびその用途
MXPA00011184A (en)	2001-09-07	Thienopyridine compounds, their production and use
CZ20004706A3 (cs)	2001-03-14	Thienopyridinové sloučeniny, způsob jejich výroby a použití
JP2000219690A (ja)	2000-08-08	チエノピリジン誘導体、その製造法および用途