SK11622003A3 - Chinolínové, izochinolínové a ftalazínové deriváty ako antagonisty gonádoliberínu - Google Patents

Chinolínové, izochinolínové a ftalazínové deriváty ako antagonisty gonádoliberínu Download PDF

Info

Publication number: SK11622003A3
Authority: SK; Slovakia
Prior art keywords: compound; group; ethyl; formula; atom
Prior art date: 2001-02-21

Application number

SK1162-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Peter Strehlke

Peter Droescher

Ulrich Buehmann

Norbert Schmees

Peter Peter Muhn

Holger Hess-Stumpp

Roland Kuehne

Eckhard Guenther

Emmanuel Polymeropoulos

Laak Antonius Marinus Ter

Original Assignee

Zentaris Gmbh

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.)

2001-02-21

Filing date

2002-02-21

Publication date

2004-01-08

2001-02-21 Priority claimed from DE2001108271 external-priority patent/DE10108271A1/de

2002-02-21 Application filed by Zentaris Gmbh filed Critical Zentaris Gmbh

2004-01-08 Publication of SK11622003A3 publication Critical patent/SK11622003A3/sk

Links

101000857870 Squalus acanthias Gonadoliberin Proteins 0.000 title claims abstract description 11
239000005557 antagonist Substances 0.000 title claims abstract description 6
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title abstract description 6
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 title abstract description 6
LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 title abstract description 3
239000000579 Gonadotropin-Releasing Hormone Substances 0.000 title abstract 2
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 title abstract 2
229940035638 gonadotropin-releasing hormone Drugs 0.000 title abstract 2
150000001875 compounds Chemical class 0.000 claims description 95
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
125000005843 halogen group Chemical group 0.000 claims description 22
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
229910052751 metal Chemical group 0.000 claims description 13
239000002184 metal Chemical group 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
NMJREATYWWNIKX-UHFFFAOYSA-N GnRH Chemical compound C1CCC(C(=O)NCC(N)=O)N1C(=O)C(CC(C)C)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)CNC(=O)C(NC(=O)C(CO)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C(CC=1NC=NC=1)NC(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 NMJREATYWWNIKX-UHFFFAOYSA-N 0.000 claims description 9
125000004429 atom Chemical group 0.000 claims description 8
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
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230000035558 fertility Effects 0.000 claims description 6
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238000000034 method Methods 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 5
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
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125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
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ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
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239000003054 catalyst Substances 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
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-1 nheptyl Chemical group 0.000 description 118
125000000217 alkyl group Chemical group 0.000 description 47
125000004432 carbon atom Chemical group C* 0.000 description 32
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
239000000203 mixture Substances 0.000 description 23
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
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239000000243 solution Substances 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
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229940121381 gonadotrophin releasing hormone (gnrh) antagonists Drugs 0.000 description 12
150000003254 radicals Chemical class 0.000 description 12
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239000005556 hormone Substances 0.000 description 6
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239000011734 sodium Substances 0.000 description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
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RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 5
125000001624 naphthyl group Chemical group 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
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229910052708 sodium Inorganic materials 0.000 description 5
229910052717 sulfur Inorganic materials 0.000 description 5
230000002483 superagonistic effect Effects 0.000 description 5
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
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YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
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239000003098 androgen Substances 0.000 description 4
229910052792 caesium Inorganic materials 0.000 description 4
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201000010099 disease Diseases 0.000 description 4
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229910052744 lithium Inorganic materials 0.000 description 4
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235000011152 sodium sulphate Nutrition 0.000 description 4
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125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 3
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LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
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YQVCFXCUPARAFI-UHFFFAOYSA-N propan-2-yl 6-(5-acetamidothiophen-2-yl)-5-[[benzyl(methyl)amino]methyl]-1-[(2,6-difluorophenyl)methyl]-4-oxoquinoline-3-carboxylate Chemical compound C12=CC=C(C=3SC(NC(C)=O)=CC=3)C(CN(C)CC=3C=CC=CC=3)=C2C(=O)C(C(=O)OC(C)C)=CN1CC1=C(F)C=CC=C1F YQVCFXCUPARAFI-UHFFFAOYSA-N 0.000 description 1
RAFDAZRPSLOXSQ-UHFFFAOYSA-N propan-2-yl 6-(6-acetamidopyridin-3-yl)-5-[[benzyl(methyl)amino]methyl]-1-[(2,6-difluorophenyl)methyl]-4-oxoquinoline-3-carboxylate Chemical compound C12=CC=C(C=3C=NC(NC(C)=O)=CC=3)C(CN(C)CC=3C=CC=CC=3)=C2C(=O)C(C(=O)OC(C)C)=CN1CC1=C(F)C=CC=C1F RAFDAZRPSLOXSQ-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
MQDVUDAZJMZQMF-UHFFFAOYSA-N pyridin-2-ylurea Chemical compound NC(=O)NC1=CC=CC=N1 MQDVUDAZJMZQMF-UHFFFAOYSA-N 0.000 description 1
125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
DJXNJVFEFSWHLY-UHFFFAOYSA-M quinoline-3-carboxylate Chemical compound C1=CC=CC2=CC(C(=O)[O-])=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-M 0.000 description 1
150000003248 quinolines Chemical class 0.000 description 1
GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 description 1
229960004622 raloxifene Drugs 0.000 description 1
230000004044 response Effects 0.000 description 1
238000004007 reversed phase HPLC Methods 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
238000007790 scraping Methods 0.000 description 1
208000008742 seborrheic dermatitis Diseases 0.000 description 1
239000013049 sediment Substances 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
230000021595 spermatogenesis Effects 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000010257 thawing Methods 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
NNBZCPXTIHJBJL-UHFFFAOYSA-N trans-decahydronaphthalene Natural products C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 1
201000007954 uterine fibroid Diseases 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
238000003466 welding Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- 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
- A61P5/02—Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin
- 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
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
- C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Endocrinology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Reproductive Health (AREA)
Gynecology & Obstetrics (AREA)
Diabetes (AREA)
Pregnancy & Childbirth (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Quinoline Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

SK1162-2003A 2001-02-21 2002-02-21 Chinolínové, izochinolínové a ftalazínové deriváty ako antagonisty gonádoliberínu SK11622003A3 (sk)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE2001108271 DE10108271A1 (de)	2001-02-21	2001-02-21	Chinolin-, Isochinolin- und Phthalazinderivate als Antagonisten des Gonadotropin freisetzenden Hormons
US27491401P	2001-03-13	2001-03-13
PCT/EP2002/001882 WO2002066437A1 (de)	2001-02-21	2002-02-21	Chinolin-, isochinolin- und phthalazinderivate als antagonisten des gonadotropin freisetzenden hormons

Publications (1)

Publication Number	Publication Date
SK11622003A3 true SK11622003A3 (sk)	2004-01-08

Family

ID=26008581

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1162-2003A SK11622003A3 (sk)	2001-02-21	2002-02-21	Chinolínové, izochinolínové a ftalazínové deriváty ako antagonisty gonádoliberínu

Country Status (17)

Country	Link
EP (1)	EP1362034A1 (ru)
JP (1)	JP2004528298A (ru)
CN (1)	CN1496354A (ru)
AU (1)	AU2002247737B2 (ru)
BG (1)	BG108165A (ru)
BR (1)	BR0207451A (ru)
CA (1)	CA2438709A1 (ru)
CZ (1)	CZ20032514A3 (ru)
HU (1)	HUP0303219A2 (ru)
IL (1)	IL157303A0 (ru)
MX (1)	MXPA03007348A (ru)
NO (1)	NO325675B1 (ru)
NZ (1)	NZ527597A (ru)
PL (1)	PL367285A1 (ru)
RU (1)	RU2280031C2 (ru)
SK (1)	SK11622003A3 (ru)
WO (1)	WO2002066437A1 (ru)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BR112015023328A2 (pt)	2013-03-13	2017-07-18	Flatley Discovery Lab	compostos de piridazinona e métodos para o tratamento de fibrose cística

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4120646A1 (de) *	1991-06-22	1992-12-24	Bayer Ag	7-isoindolinyl-chinolon- und naphthyridoncarbonsaeure-derivate
ATE223902T1 (de) *	1995-10-19	2002-09-15	Takeda Chemical Industries Ltd	Chinolinderivate als gnrh antagonisten
WO1997044041A1 (en) *	1996-05-20	1997-11-27	Merck & Co., Inc.	Antagonists of gonadotropin releasing hormone

2002
- 2002-02-21 NZ NZ527597A patent/NZ527597A/en unknown
- 2002-02-21 AU AU2002247737A patent/AU2002247737B2/en not_active Ceased
- 2002-02-21 CN CNA028063597A patent/CN1496354A/zh active Pending
- 2002-02-21 CZ CZ20032514A patent/CZ20032514A3/cs unknown
- 2002-02-21 HU HU0303219A patent/HUP0303219A2/hu unknown
- 2002-02-21 PL PL02367285A patent/PL367285A1/xx not_active Application Discontinuation
- 2002-02-21 WO PCT/EP2002/001882 patent/WO2002066437A1/de not_active Ceased
- 2002-02-21 IL IL15730302A patent/IL157303A0/xx unknown
- 2002-02-21 RU RU2003128647/04A patent/RU2280031C2/ru not_active IP Right Cessation
- 2002-02-21 JP JP2002565954A patent/JP2004528298A/ja active Pending
- 2002-02-21 CA CA002438709A patent/CA2438709A1/en not_active Abandoned
- 2002-02-21 BR BR0207451-6A patent/BR0207451A/pt not_active IP Right Cessation
- 2002-02-21 EP EP02716803A patent/EP1362034A1/de not_active Withdrawn
- 2002-02-21 MX MXPA03007348A patent/MXPA03007348A/es active IP Right Grant
- 2002-02-21 SK SK1162-2003A patent/SK11622003A3/sk unknown
2003
- 2003-08-20 NO NO20033698A patent/NO325675B1/no not_active IP Right Cessation
- 2003-09-09 BG BG108165A patent/BG108165A/xx unknown

Also Published As

Publication number	Publication date
MXPA03007348A (es)	2003-12-04
PL367285A1 (en)	2005-02-21
RU2280031C2 (ru)	2006-07-20
RU2003128647A (ru)	2005-03-27
AU2002247737B2 (en)	2006-05-18
CA2438709A1 (en)	2002-08-29
IL157303A0 (en)	2004-02-19
NO20033698L (no)	2003-10-20
NO20033698D0 (no)	2003-08-20
NO325675B1 (no)	2008-07-07
JP2004528298A (ja)	2004-09-16
CZ20032514A3 (cs)	2004-05-12
WO2002066437A1 (de)	2002-08-29
HUP0303219A2 (hu)	2003-12-29
BG108165A (en)	2004-08-31
EP1362034A1 (de)	2003-11-19
BR0207451A (pt)	2004-06-01
CN1496354A (zh)	2004-05-12
NZ527597A (en)	2004-10-29

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Date	Code	Title	Description
2010-10-07	FB9A	Suspension of patent application procedure