OA11568A - Thienopyridine compounds, their production and use. - Google Patents

Thienopyridine compounds, their production and use. Download PDF

Info

Publication number: OA11568A
Authority: OA; OAPI
Prior art keywords: substituted; group; compound; sait; alkoxy
Prior art date: 1998-06-26

Application number

OA1200000345A

Other languages

English (en)

Inventor

Choh Nobuo

Furuya Shuichi

Imada Takashi

Suzuki Nobuhiro

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.)

1998-06-26

Filing date

1999-06-24

Publication date

2004-07-26

1999-06-24 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

2004-07-26 Publication of OA11568A publication Critical patent/OA11568A/en

Links

238000004519 manufacturing process Methods 0.000 title description 56
DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical class C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 223
101000857870 Squalus acanthias Gonadoliberin Proteins 0.000 claims abstract description 13
239000000579 Gonadotropin-Releasing Hormone Substances 0.000 claims abstract description 9
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 claims abstract description 9
229940035638 gonadotropin-releasing hormone Drugs 0.000 claims abstract description 8
230000003042 antagnostic effect Effects 0.000 claims abstract description 6
201000010099 disease Diseases 0.000 claims abstract description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 6
239000003163 gonadal steroid hormone Substances 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims description 65
-1 C3_3acyl Chemical group 0.000 claims description 63
125000001424 substituent group Chemical group 0.000 claims description 57
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 42
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 30
125000000033 alkoxyamino group Chemical group 0.000 claims description 26
238000000034 method Methods 0.000 claims description 26
125000003545 alkoxy group Chemical group 0.000 claims description 24
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 21
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 21
125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims description 15
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 14
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
125000004423 acyloxy group Chemical group 0.000 claims description 12
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 12
125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 12
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 12
239000008194 pharmaceutical composition Substances 0.000 claims description 10
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 8
239000000546 pharmaceutical excipient Substances 0.000 claims description 8
125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 7
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 6
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 6
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
241000124008 Mammalia Species 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
239000003488 releasing hormone Substances 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims description 2
RKOZBCHRMRTGBD-UHFFFAOYSA-N n-[4-[3-[[benzyl(methyl)amino]methyl]-7-[(2,6-difluorophenyl)methyl]-5-(2-methylpropanoyl)-4-oxothieno[2,3-b]pyridin-2-yl]phenyl]cyclopropanecarboxamide Chemical compound C1=2SC(C=3C=CC(NC(=O)C4CC4)=CC=3)=C(CN(C)CC=3C=CC=CC=3)C=2C(=O)C(C(=O)C(C)C)=CN1CC1=C(F)C=CC=C1F RKOZBCHRMRTGBD-UHFFFAOYSA-N 0.000 claims description 2
125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
229940125810 compound 20 Drugs 0.000 claims 1
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
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201000009273 Endometriosis Diseases 0.000 abstract description 5
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206010006187 Breast cancer Diseases 0.000 abstract description 4
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239000003433 contraceptive agent Substances 0.000 abstract description 2
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208000000509 infertility Diseases 0.000 abstract description 2
230000036512 infertility Effects 0.000 abstract description 2
231100000535 infertility Toxicity 0.000 abstract description 2
210000001672 ovary Anatomy 0.000 abstract description 2
230000035935 pregnancy Effects 0.000 abstract description 2
230000001419 dependent effect Effects 0.000 abstract 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 73
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 71
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
239000000243 solution Substances 0.000 description 62
239000002904 solvent Substances 0.000 description 51
230000002829 reductive effect Effects 0.000 description 45
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 44
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 38
238000005160 1H NMR spectroscopy Methods 0.000 description 35
238000001816 cooling Methods 0.000 description 35
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
239000000203 mixture Substances 0.000 description 33
239000011541 reaction mixture Substances 0.000 description 31
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FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 27
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
238000000921 elemental analysis Methods 0.000 description 25
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
239000000843 powder Substances 0.000 description 22
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239000012044 organic layer Substances 0.000 description 20
235000019341 magnesium sulphate Nutrition 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
101150041968 CDC13 gene Proteins 0.000 description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
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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 10
239000012528 membrane Substances 0.000 description 10
229920006395 saturated elastomer Polymers 0.000 description 10
239000007858 starting material Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 8
239000007787 solid Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
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AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 7
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235000002906 tartaric acid Nutrition 0.000 description 1
210000001550 testis Anatomy 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
238000010257 thawing Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
229940125670 thienopyridine Drugs 0.000 description 1
239000002175 thienopyridine Substances 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
235000010215 titanium dioxide Nutrition 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
239000013638 trimer Substances 0.000 description 1
JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
VXKHXGOKWPXYNA-PGBVPBMZSA-N triptorelin Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=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 VXKHXGOKWPXYNA-PGBVPBMZSA-N 0.000 description 1
229960004824 triptorelin Drugs 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
238000005199 ultracentrifugation Methods 0.000 description 1
239000006216 vaginal suppository Substances 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000008215 water for injection 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
- 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
- A61P35/00—Antineoplastic agents
- 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
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones

Landscapes

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

OA1200000345A 1998-06-26 1999-06-24 Thienopyridine compounds, their production and use. OA11568A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP18126398		1998-06-26
JP33300498		1998-11-24

Publications (1)

Publication Number	Publication Date
OA11568A true OA11568A (en)	2004-07-26

Family

ID=26500516

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200000345A OA11568A (en)	1998-06-26	1999-06-24	Thienopyridine compounds, their production and use.

Country Status (10)

Country	Link
US (1)	US6329388B2 (id)
JP (1)	JP2000219691A (id)
KR (2)	KR20010020155A (id)
CN (1)	CN1306535A (id)
AR (1)	AR018935A1 (id)
ID (1)	ID26780A (id)
OA (1)	OA11568A (id)
PL (1)	PL345074A1 (id)
TR (1)	TR200003784T2 (id)
TW (1)	TW430665B (id)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1291023A1 (en) *	2000-06-14	2003-03-12	Takeda Chemical Industries, Ltd.	Sustained release compositions
US7569570B2 (en)	2002-01-30	2009-08-04	Takeda Pharmaceutical Company Limited	Thienopyrimidines, process for preparing the same and use thereof
US20050250793A1 (en) *	2002-04-12	2005-11-10	Masami Kusaka	Preventives/remedies for hot flash
CN101684123B (zh) *	2008-09-27	2013-12-11	四川大学	2-甲酰胺基噻吩并吡啶衍生物制备方法及医药用途
CN117343073B (zh) *	2022-06-28	2025-11-14	上海汇伦医药股份有限公司	含噻吩并环类衍生物、其制备方法及其在医药上的应用

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
JPH09169766A (ja)	1995-10-19	1997-06-30	Takeda Chem Ind Ltd	チエノピリジン誘導体，その製造法および用途
EP0781774B1 (en) *	1995-12-08	2002-07-31	Takeda Chemical Industries, Ltd.	Prolactin production inhibitory agents
WO1997041126A1 (en)	1996-04-26	1997-11-06	Takeda Chemical Industries, Ltd.	Thienopyridine derivatives, their production and use

1999
- 1999-06-24 ID IDW20002716A patent/ID26780A/id unknown
- 1999-06-24 OA OA1200000345A patent/OA11568A/en unknown
- 1999-06-24 AR ARP990103031A patent/AR018935A1/es unknown
- 1999-06-24 KR KR1019997009714A patent/KR20010020155A/ko not_active Abandoned
- 1999-06-24 TW TW088110611A patent/TW430665B/zh active
- 1999-06-24 CN CN99807793A patent/CN1306535A/zh active Pending
- 1999-06-24 PL PL99345074A patent/PL345074A1/xx unknown
- 1999-06-24 TR TR2000/03784T patent/TR200003784T2/xx unknown
- 1999-09-28 JP JP11273754A patent/JP2000219691A/ja not_active Withdrawn
- 1999-10-21 KR KR1019990709751A patent/KR20000012154A/ko not_active Abandoned
2000
- 2000-12-14 US US09/736,641 patent/US6329388B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
JP2000219691A (ja)	2000-08-08
CN1306535A (zh)	2001-08-01
ID26780A (id)	2001-02-08
KR20000012154A (ko)	2000-02-25
KR20010020155A (ko)	2001-03-15
US20010001104A1 (en)	2001-05-10
TW430665B (en)	2001-04-21
US6329388B2 (en)	2001-12-11
AR018935A1 (es)	2001-12-12
TR200003784T2 (tr)	2001-06-21
PL345074A1 (en)	2001-12-03

Publication	Publication Date	Title
CA2368108C (en)	2009-12-22	Thienopyrimidine compounds, their production and use
JP3789538B2 (ja)	2006-06-28	チエノピリミジン誘導体、その製造法および用途
CN1146206A (zh)	1997-03-26	双环噻吩衍生物及其作为促性腺激素释放激素拮抗剂的应用
KR20050099525A (ko)	2005-10-13	피롤로트리아진 키나제 억제제의 제조 방법
US6297379B1 (en)	2001-10-02	Thienopyrimidine compounds, their production and use
JP2005501858A (ja)	2005-01-20	オキシトシン作動薬としてのジアザシクロアルカン
US6262267B1 (en)	2001-07-17	Thienopyridine compound
OA11568A (en)	2004-07-26	Thienopyridine compounds, their production and use.
US6297255B1 (en)	2001-10-02	Thienopyridine compounds, their production and use
JP3854648B2 (ja)	2006-12-06	縮合チオフェン誘導体、その製造法及び用途
JP3028486B1 (ja)	2000-04-04	チエノピリジン誘導体、その製造法および用途
JP4652520B2 (ja)	2011-03-16	チエノピリミジン化合物、その製造法および用途
ZA200006601B (en)	2001-11-14	Thienopyridine compounds, their production and use.
MXPA00011184A (en)	2001-09-07	Thienopyridine compounds, their production and use
CZ20004706A3 (cs)	2001-03-14	Thienopyridinové sloučeniny, způsob jejich výroby a použití