NO328826B1 - Bicykliske heteroaromatiske forbindelser anvendelige som LH-agonister samt farmasoytiske preparater inneholdende slike - Google Patents
Bicykliske heteroaromatiske forbindelser anvendelige som LH-agonister samt farmasoytiske preparater inneholdende slike Download PDFInfo
- Publication number
- NO328826B1 NO328826B1 NO20014824A NO20014824A NO328826B1 NO 328826 B1 NO328826 B1 NO 328826B1 NO 20014824 A NO20014824 A NO 20014824A NO 20014824 A NO20014824 A NO 20014824A NO 328826 B1 NO328826 B1 NO 328826B1
- Authority
- NO
- Norway
- Prior art keywords
- amino
- methylthio
- silica gel
- dichloromethane
- ethyl
- Prior art date
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- -1 Bicyclic heteroaromatic compounds Chemical class 0.000 title claims description 23
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 11
- 239000000556 agonist Substances 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 76
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 4
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 230000035558 fertility Effects 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 279
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- 229910002027 silica gel Inorganic materials 0.000 description 108
- 238000000034 method Methods 0.000 description 70
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 68
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- 239000003480 eluent Substances 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 38
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 32
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- PVBRSNZAOAJRKO-UHFFFAOYSA-N ethyl 2-sulfanylacetate Chemical compound CCOC(=O)CS PVBRSNZAOAJRKO-UHFFFAOYSA-N 0.000 description 23
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- NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 14
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- 125000004432 carbon atom Chemical group C* 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
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- 150000001408 amides Chemical class 0.000 description 10
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 9
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- 108020004414 DNA Proteins 0.000 description 6
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- 108010086677 Gonadotropins Proteins 0.000 description 6
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
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- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
- ZPHGMBGIFODUMF-UHFFFAOYSA-N thiophen-2-ylmethanol Chemical compound OCC1=CC=CS1 ZPHGMBGIFODUMF-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
- 238000001890 transfection Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—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
- A61P15/16—Masculine 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
- A61P15/18—Feminine contraceptives
-
- 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
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Endocrinology (AREA)
- Public Health (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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP99201152 | 1999-04-08 | ||
PCT/EP2000/002865 WO2000061586A1 (en) | 1999-04-08 | 2000-04-03 | Bicyclic heteroaromatic compounds useful as lh agonists |
Publications (3)
Publication Number | Publication Date |
---|---|
NO20014824D0 NO20014824D0 (no) | 2001-10-04 |
NO20014824L NO20014824L (no) | 2001-10-04 |
NO328826B1 true NO328826B1 (no) | 2010-05-25 |
Family
ID=8240094
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20014824A NO328826B1 (no) | 1999-04-08 | 2001-10-04 | Bicykliske heteroaromatiske forbindelser anvendelige som LH-agonister samt farmasoytiske preparater inneholdende slike |
Country Status (30)
Country | Link |
---|---|
US (2) | US6569863B1 (cs) |
EP (1) | EP1171443B1 (cs) |
JP (1) | JP4854856B2 (cs) |
KR (1) | KR100691546B1 (cs) |
CN (1) | CN1177848C (cs) |
AR (1) | AR028474A1 (cs) |
AT (1) | ATE299507T1 (cs) |
AU (1) | AU772258B2 (cs) |
BR (1) | BRPI0009558B1 (cs) |
CA (1) | CA2368834C (cs) |
CO (1) | CO5160348A1 (cs) |
CZ (1) | CZ300832B6 (cs) |
DE (1) | DE60021262T2 (cs) |
DK (1) | DK1171443T3 (cs) |
ES (1) | ES2245304T3 (cs) |
HK (1) | HK1041266B (cs) |
HU (1) | HU229002B1 (cs) |
ID (1) | ID30502A (cs) |
IL (2) | IL145483A0 (cs) |
MX (1) | MXPA01010144A (cs) |
NO (1) | NO328826B1 (cs) |
NZ (1) | NZ514445A (cs) |
PE (1) | PE20010030A1 (cs) |
PL (1) | PL219316B1 (cs) |
PT (1) | PT1171443E (cs) |
RU (1) | RU2248979C2 (cs) |
TR (1) | TR200102839T2 (cs) |
TW (1) | TW564247B (cs) |
WO (1) | WO2000061586A1 (cs) |
ZA (1) | ZA200107917B (cs) |
Families Citing this family (44)
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PT1322651E (pt) | 2000-09-22 | 2008-02-28 | Organon Nv | Compostos heteroaromáticos bicíclicos |
GB0100622D0 (en) | 2001-01-10 | 2001-02-21 | Vernalis Res Ltd | Chemical compounds V111 |
DE10108481A1 (de) * | 2001-02-22 | 2002-10-24 | Bayer Ag | Pyridylpyrimidine |
JP4263094B2 (ja) | 2001-09-04 | 2009-05-13 | ナームローゼ・フエンノートチヤツプ・オルガノン | LH及びFSH合併アゴニスト作用を有するグリシン置換チエノ[2,3−d]ピリミジン |
TWI228508B (en) * | 2001-09-04 | 2005-03-01 | Akzo Nobel Nv | Thieno[2,3-d]pyrimidines with combined LH and FSH agonistic activity |
ME00355B (me) | 2002-06-06 | 2010-06-30 | Ptp Group Ltd | Kristalisan polietilen tereftalat, koji sadrži silicijum, i postupak za njegovo dobijanje |
US6974870B2 (en) | 2002-06-06 | 2005-12-13 | Boehringer Ingelheim Phamaceuticals, Inc. | Substituted 3-amino-thieno [2,3-b]pyridine-2-carboxylic acid amide compounds and processes for preparing and their uses |
EP1633756B1 (en) | 2003-04-09 | 2008-12-24 | Biogen Idec MA Inc. | A2a adenosine receptor antagonists |
US7674791B2 (en) | 2003-04-09 | 2010-03-09 | Biogen Idec Ma Inc. | Triazolopyrazines and methods of making and using the same |
WO2004092170A2 (en) | 2003-04-09 | 2004-10-28 | Biogen Idec Ma Inc. | Triazolotriazines and pyrazolotriazines useful as a2a adenosine receptor antagon ists |
JPWO2005019225A1 (ja) * | 2003-08-21 | 2007-11-01 | 杏林製薬株式会社 | Nk1受容体拮抗作用を有する化合物の製造方法及びその製造中間体 |
US7550485B2 (en) * | 2003-10-14 | 2009-06-23 | Wyeth | Substituted N-heterocycle derivatives and methods of their use |
US7816353B2 (en) * | 2003-10-24 | 2010-10-19 | Exelixis, Inc. | P70S6 kinase modulators and method of use |
US7781478B2 (en) | 2004-07-14 | 2010-08-24 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
US7645881B2 (en) * | 2004-07-22 | 2010-01-12 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
EP1962892A4 (en) * | 2005-11-22 | 2011-10-12 | Univ South Florida | INHIBITION OF CELL PROLIFERATION |
AR059898A1 (es) | 2006-03-15 | 2008-05-07 | Janssen Pharmaceutica Nv | Derivados de 3-ciano-piridona 1,4-disustituida y su uso como moduladores alostericos de los receptores mglur2 |
JP2009537551A (ja) * | 2006-05-17 | 2009-10-29 | アメリカ合衆国 | ホルモン受容体を調節するためのピリミジン低分子量リガンド |
US7592353B2 (en) | 2006-06-06 | 2009-09-22 | Boehringer Ingelheim International Gmbh | Substituted 3-amino-thieno[2,3-b]pyridine-2-carboxylic acid amide compounds and processes for preparing and their uses |
RU2444524C2 (ru) * | 2006-08-21 | 2012-03-10 | Дженентек, Инк. | Азабензотиофенильные соединения и способы применения |
TW200900065A (en) | 2007-03-07 | 2009-01-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives |
TW200845978A (en) | 2007-03-07 | 2008-12-01 | Janssen Pharmaceutica Nv | 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives |
CN101801930B (zh) * | 2007-09-14 | 2013-01-30 | 奥梅-杨森制药有限公司 | 1,3-二取代的-4-苯基-1h-吡啶-2-酮 |
BRPI0816767B8 (pt) | 2007-09-14 | 2021-05-25 | Addex Pharmaceuticals Sa | composto 4-fenil-3,4,5,6-tetra-hidro-2h,1'h-[1,4']bipiridi¬nil-2'-onas 1',3'-dissubstituídas, composição farmacêutica e uso dos mesmos |
AU2008297876B2 (en) | 2007-09-14 | 2011-07-07 | Addex Pharma S.A. | 1,3-disubstituted 4-(aryl-x-phenyl)-1h-pyridin-2-ones |
RU2528340C2 (ru) * | 2007-10-18 | 2014-09-10 | Бёрингер Ингельхайм Интернациональ Гмбх | ПОЛУЧЕНИЕ ДИГИДРОТИЕНО[3,2-d]ПИРИМИДИНОВ И ПРОМЕЖУТОЧНЫХ ПРОДУКТОВ, ПРИМЕНЯЮЩИХСЯ ДЛЯ ИХ СИНТЕЗА |
ES2637794T3 (es) | 2007-11-14 | 2017-10-17 | Janssen Pharmaceuticals, Inc. | Derivados de imidazo[1,2-A]piridina y su uso como moduladores alostéricos positivos de receptores MGLUR2 |
AU2009289784B2 (en) | 2008-09-02 | 2012-03-22 | Addex Pharma S.A. | 3-azabicyclo[3.1.0]hexyl derivatives as modulators of metabotropic glutamate receptors |
WO2010043396A1 (en) | 2008-10-16 | 2010-04-22 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | Indole and benzomorpholine derivatives as modulators of metabotropic glutamate receptors |
WO2010060589A1 (en) | 2008-11-28 | 2010-06-03 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | Indole and benzoxazine derivatives as modulators of metabotropic glutamate receptors |
US8946205B2 (en) | 2009-05-12 | 2015-02-03 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
MY161325A (en) | 2009-05-12 | 2017-04-14 | Janssen Pharmaceuticals Inc | 1, 2, 4-triazolo[4,3-a]pyridine derivatives and their use for the treatment or prevention of neurological and psychiatric disorders |
MY153913A (en) | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
PL2649069T3 (pl) | 2010-11-08 | 2016-01-29 | Janssen Pharmaceuticals Inc | Pochodne 1,2,4-triazolo[4,3-a]pirydyny i ich zastosowanie jako dodatnich allosterycznych modulatorów receptorów mGluR2 |
AU2011328203B2 (en) | 2010-11-08 | 2015-03-19 | Janssen Pharmaceuticals, Inc. | 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors |
CN103261195B (zh) | 2010-11-08 | 2015-09-02 | 杨森制药公司 | 1,2,4-三唑并[4,3-a]吡啶衍生物及其作为MGLUR2受体的正变构调节剂的用途 |
EP2734239A2 (en) | 2011-07-18 | 2014-05-28 | Arts Biologics A/S | Long acting luteinizing hormone (lh) compound |
EP3048106B1 (en) | 2011-11-23 | 2019-11-06 | Cancer Research Technology Limited | Thienopyrimidine as inhibitors of atypical protein kinase c |
JO3368B1 (ar) | 2013-06-04 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2 |
JO3367B1 (ar) | 2013-09-06 | 2019-03-13 | Janssen Pharmaceutica Nv | مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2 |
UA121965C2 (uk) | 2014-01-21 | 2020-08-25 | Янссен Фармацевтика Нв | Комбінації, які містять позитивні алостеричні модулятори або ортостеричні агоністи метаботропного глутаматергічного рецептора 2 підтипу, та їх застосування |
KR102461134B1 (ko) | 2014-01-21 | 2022-10-28 | 얀센 파마슈티카 엔.브이. | 대사 조절형 글루탐산 작동성 수용체 제2아형의 양성 알로스테릭 조절제 또는 오르토스테릭 작동제를 포함하는 조합 및 그 용도 |
CN107602585A (zh) * | 2017-10-23 | 2018-01-19 | 遵义医学院 | 噻吩并吡啶双杂环化合物的制备工艺 |
BR102019022529A2 (pt) * | 2019-10-25 | 2021-05-04 | Anhanguera Educacional Ltda. | Processo para obtenção de composições farmacêuticas antitumorais através de butadienos push-pull, compostos e seus usos |
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Publication number | Priority date | Publication date | Assignee | Title |
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WO1993013664A2 (en) | 1992-01-11 | 1993-07-22 | Schering Agrochemicals Limited | Biheterocyclic fungicidal compounds |
TW449600B (en) | 1994-04-19 | 2001-08-11 | Takeda Chemical Industries Ltd | Condensed-ring thiophene derivatives, their production and use |
JP3854648B2 (ja) * | 1994-04-19 | 2006-12-06 | 武田薬品工業株式会社 | 縮合チオフェン誘導体、その製造法及び用途 |
ATE225351T1 (de) * | 1994-11-08 | 2002-10-15 | Takeda Chemical Industries Ltd | Thienopyridin und thienopyrimidinderivate und ihre verwendung als entzündungshemmende mittel |
WO1997014697A1 (en) | 1995-10-19 | 1997-04-24 | Takeda Chemical Industries, Ltd. | Thienopyridine derivatives as gonadotropin releasing hormone antagonists |
JPH09169767A (ja) * | 1995-10-19 | 1997-06-30 | Takeda Chem Ind Ltd | 複素環化合物、その製造法および用途 |
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 |
WO1997041126A1 (en) | 1996-04-26 | 1997-11-06 | Takeda Chemical Industries, Ltd. | Thienopyridine derivatives, their production and use |
-
2000
- 2000-03-23 TW TW089105361A patent/TW564247B/zh not_active IP Right Cessation
- 2000-04-03 CA CA002368834A patent/CA2368834C/en not_active Expired - Fee Related
- 2000-04-03 PL PL350964A patent/PL219316B1/pl unknown
- 2000-04-03 AT AT00917026T patent/ATE299507T1/de active
- 2000-04-03 DK DK00917026T patent/DK1171443T3/da active
- 2000-04-03 CN CNB008069077A patent/CN1177848C/zh not_active Expired - Fee Related
- 2000-04-03 AU AU38166/00A patent/AU772258B2/en not_active Ceased
- 2000-04-03 PT PT00917026T patent/PT1171443E/pt unknown
- 2000-04-03 KR KR1020017012792A patent/KR100691546B1/ko not_active IP Right Cessation
- 2000-04-03 RU RU2001130051/04A patent/RU2248979C2/ru not_active IP Right Cessation
- 2000-04-03 ES ES00917026T patent/ES2245304T3/es not_active Expired - Lifetime
- 2000-04-03 WO PCT/EP2000/002865 patent/WO2000061586A1/en active IP Right Grant
- 2000-04-03 EP EP00917026A patent/EP1171443B1/en not_active Expired - Lifetime
- 2000-04-03 MX MXPA01010144A patent/MXPA01010144A/es active IP Right Grant
- 2000-04-03 BR BRPI0009558A patent/BRPI0009558B1/pt not_active IP Right Cessation
- 2000-04-03 NZ NZ514445A patent/NZ514445A/en not_active IP Right Cessation
- 2000-04-03 JP JP2000610857A patent/JP4854856B2/ja not_active Expired - Fee Related
- 2000-04-03 US US09/937,416 patent/US6569863B1/en not_active Expired - Lifetime
- 2000-04-03 TR TR2001/02839T patent/TR200102839T2/xx unknown
- 2000-04-03 IL IL14548300A patent/IL145483A0/xx active IP Right Grant
- 2000-04-03 HU HU0200653A patent/HU229002B1/hu not_active IP Right Cessation
- 2000-04-03 DE DE60021262T patent/DE60021262T2/de not_active Expired - Lifetime
- 2000-04-03 CZ CZ20013605A patent/CZ300832B6/cs not_active IP Right Cessation
- 2000-04-03 ID IDW00200102449A patent/ID30502A/id unknown
- 2000-04-06 AR ARP000101578A patent/AR028474A1/es not_active Application Discontinuation
- 2000-04-06 PE PE2000000312A patent/PE20010030A1/es not_active Application Discontinuation
- 2000-04-07 CO CO00025852A patent/CO5160348A1/es unknown
-
2001
- 2001-09-16 IL IL145483A patent/IL145483A/en not_active IP Right Cessation
- 2001-09-26 ZA ZA200107917A patent/ZA200107917B/xx unknown
- 2001-10-04 NO NO20014824A patent/NO328826B1/no not_active IP Right Cessation
-
2002
- 2002-04-23 HK HK02103025.1A patent/HK1041266B/zh not_active IP Right Cessation
-
2003
- 2003-04-11 US US10/411,960 patent/US6841553B2/en not_active Expired - Lifetime
Also Published As
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JP4262092B2 (ja) | LH作動活性とFSH作動活性を合わせ持つチエノ[2,3−d]ピリミジン誘導体 | |
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Owner name: MERCK SHARP & DOHME BV, NL |
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MM1K | Lapsed by not paying the annual fees |