AR035855A1 - Derivados de quinolina , isoquinolina y ftalazina como antagonistas de la hormona que libera la gonadotropina y un metodo para su preparacion - Google Patents
Derivados de quinolina , isoquinolina y ftalazina como antagonistas de la hormona que libera la gonadotropina y un metodo para su preparacionInfo
- Publication number
- AR035855A1 AR035855A1 ARP020100588A ARP020100588A AR035855A1 AR 035855 A1 AR035855 A1 AR 035855A1 AR P020100588 A ARP020100588 A AR P020100588A AR P020100588 A ARP020100588 A AR P020100588A AR 035855 A1 AR035855 A1 AR 035855A1
- Authority
- AR
- Argentina
- Prior art keywords
- group
- optionally substituted
- alkyl
- hydrogen atom
- halogen atoms
- Prior art date
Links
- 239000005557 antagonist Substances 0.000 title abstract 2
- 239000005556 hormone Substances 0.000 title abstract 2
- 229940088597 hormone Drugs 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 16
- 125000005843 halogen group Chemical group 0.000 abstract 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 2
- 208000007984 Female Infertility Diseases 0.000 abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- 150000005840 aryl radicals Chemical group 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 229920001577 copolymer Chemical group 0.000 abstract 2
- 125000004122 cyclic group Chemical group 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- -1 phenyl- Chemical group 0.000 abstract 2
- 108090000765 processed proteins & peptides Proteins 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- 125000004434 sulfur atom Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 abstract 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 1
- 108010086677 Gonadotropins Proteins 0.000 abstract 1
- 102000006771 Gonadotropins Human genes 0.000 abstract 1
- 101000744947 Homo sapiens Zinc finger protein 213 Proteins 0.000 abstract 1
- 206010021928 Infertility female Diseases 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 abstract 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 1
- 102100039942 Zinc finger protein 213 Human genes 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
- 230000035558 fertility Effects 0.000 abstract 1
- 239000002622 gonadotropin Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 238000001794 hormone therapy Methods 0.000 abstract 1
- 230000036512 infertility Effects 0.000 abstract 1
- 231100000535 infertility Toxicity 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- 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
- 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
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- 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
-
- 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
- A61P5/26—Androgens
-
- 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
- A61P5/30—Oestrogens
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Abstract
Derivados de quinolina, isoquinolina y ftalazina de fórmula general (1) donde R1 es (a) un grupo acilo -CO-R11 ó CN, donde R11 es un radical orgánico saturado, insaturado, cíclico y/o (hetero)aromático, particularmente una cadena alquilo lineal o ramificada C1-10, o un grupo fenilo-, furano- o tiofeno sustituido opcionalmente por grupos alquilo o átomos de halógeno, (b) un grupo de éster de ácido carboxílico -CO-OR12 o un grupo de amida de ácido carboxílico -CO-NR12R13 o un grupo -SOx-R12 con x = 0, 1 ó 2, ó -SO2-NR12R13, donde R12 puede ser un radical orgánico, saturado, insaturado, cíclico y/o (hetero)aromático, particularmente una cadena alquilo lineal o ramificada C1-10, un grupo aralquilo C7-20, donde el radical arilo puede estar sustituido opcionalmente por grupos alquilo o átomos de halógeno, o un radical fenilo sustituido opcionalmente por grupos alquilo o átomos de halógeno y R13 puede ser un átomo de hidrógeno o una cadena alquilo lineal o ramificada C1-10, o (c) el grupo -A-NR14-CO-NR15R16, donde A es un grupo alquileno opcionalmente sustituido por un grupo alquilo C1-6, particularmente con 1 átomo de carbono, un grupo carbonilo, un átomo de oxígeno ó el grupo -SOx- con x = 0, 1 ó 2, R14 y R15 son, cada uno independientemente, un átomo de hidrógeno o una cadena alquilo lineal o ramificada C1-10 y R16 es una cadena alquilo lineal o ramificada C1-10, un grupo cicloalquilo C3-10, un grupo cicloalquilalquilo C7-20, un grupo aralquilo C7-20, donde el radical arilo puede estar sustituido opcionalmente por grupos alquilo o átomos de halógeno, un grupo fenilo sustituido opcionalmente por grupos alquilo o átomos de halógeno o un anillo heterocíclico sustituido opcionalmente por grupos alquilo o átomos de halógeno; R2 es un grupo -CH(R21)R22, donde R21 es un átomo de hidrógeno, un grupo alquilo C1-10 o un anillo fenilo opcionalmente sustituido y R22 es un anillo fenilo o naftilo opcionalmente sustituido, o un grupo -CH2CH(R23)R24, con R23 y R24 que significan un anillo fenilo opcionalmente sustituido; R3 y R4 pueden ser, cada uno independientemente, un átomo de hidrógeno o un grupo alquilo C1-10 y R3 también puede ser un átomo de halógeno; R5 es un grupo ligado a través del radical Z, de la fórmula (2), donde G-C=C-, -C=N-, -N=C- es un átomo de oxígeno o de azufre, Z es un enlace directo, un átomo de oxígeno o de azufre, el grupo CH-R52 o -CHR52-CH-R53-, donde R52 y R53 son, independientemente entre sí, un átomo de hidrógeno o un grupo alquilo y n significa los números 1 y 2, un enlace triple -C:::C- o es un grupo configurado en E- ó Z- CR52=CR53 ó C=CR52R53, donde R52 y R53 significan, independientemente entre sí, un átomo de hidrógeno o un grupo alquilo; L es un grupo CH2- o un grupo NH, Q es un grupo carbonilo ó -SOx con x = 0, 1 ó 2 y R51 es un grupo amino opcionalmente sustituido por un grupo alquilo o un grupo alquilo lineal o ramificado, opcionalmente sustituido por átomos de halógeno, grupos hidroxilo o alcoxi o un grupo cicloalquilo C3-7, opcionalmente sustituido por átomos de halógeno, hidroxilo o alcoxi; R6 es el grupo CH2-N(R61)R62, donde R61 es, independientemente, un átomo de hidrógeno o un grupo alquilo y R62 es un grupo alquilo o un grupo aralquilo o hetero-arilalquilo C7-20, opcionalmente sustituido, y el grupo de fórmula (3) puede significar el grupo de fórmulas (4) en cualquier orientación, y además todos los estereoisómeros de la estructura mencionada y sales de los mismos, con ácidos o bases fisiológicamente aceptables. Estos compuestos son antagonistas de la hormona que libera gonadotropina, son superiores a los compuestos peptídicos conocidos y constituyen una alternativa eficaz de los compuestos no-peptídicos conocidos. Los compuestos de fórmula (1) poseen tanto una elevada eficacia como también una gran biodisponibilidad. Además, pueden ser sintetizados de manera sencilla y lo más económica posible. Método para preparar los compuestos de fórmula (1) y uso de los mismos para controlar la fertilidad masculina, para la terapia hormonal, para el tratamiento de la subfertilidad y la infertilidad femenina, para la contracepción y para combatir tumores.
Applications Claiming Priority (1)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR035855A1 true AR035855A1 (es) | 2004-07-21 |
Family
ID=7674949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP020100588A AR035855A1 (es) | 2001-02-21 | 2002-02-21 | Derivados de quinolina , isoquinolina y ftalazina como antagonistas de la hormona que libera la gonadotropina y un metodo para su preparacion |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US6790858B2 (es) |
| KR (1) | KR100701806B1 (es) |
| AR (1) | AR035855A1 (es) |
| DE (1) | DE10108271A1 (es) |
| UA (1) | UA73409C2 (es) |
| ZA (1) | ZA200306429B (es) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100074949A1 (en) | 2008-08-13 | 2010-03-25 | William Rowe | Pharmaceutical composition and administration thereof |
| ME02970B (me) | 2004-06-24 | 2018-07-20 | Vertex Pharma | Modulatori atp-vezujućih kasetnih transportera |
| US8354427B2 (en) | 2004-06-24 | 2013-01-15 | Vertex Pharmaceutical Incorporated | Modulators of ATP-binding cassette transporters |
| JP5192389B2 (ja) * | 2005-12-05 | 2013-05-08 | メルク・シャープ・エンド・ドーム・コーポレイション | キノロンｍ１レセプター陽性アロステリックモジュレータ |
| US20090105272A1 (en) * | 2005-12-24 | 2009-04-23 | Grootenhuis Peter D J | Prodrugs of modulators of ABC transporters |
| LT1993360T (lt) | 2005-12-28 | 2017-06-12 | Vertex Pharmaceuticals Incorporated | N-[2,4-bis(1,1-dimetiletil)-5-hidroksifenil]-1,4-dihidro-4-oksochinolin-3-karboksamido kieta forma |
| EP2821400B1 (en) | 2009-03-20 | 2017-09-27 | Vertex Pharmaceuticals Incorporated | Process for making modulators of cystic fibrosis transmembrane conductance regulator |
| US8802700B2 (en) | 2010-12-10 | 2014-08-12 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding Cassette transporters |
| WO2013130669A1 (en) | 2012-02-27 | 2013-09-06 | Vertex Pharmaceuticals Incorporated | Pharmaceutical composition and administration thereof |
| BR112015023328A2 (pt) | 2013-03-13 | 2017-07-18 | Flatley Discovery Lab | compostos de piridazinona e métodos para o tratamento de fibrose cística |
| AU2015330923B2 (en) | 2014-10-07 | 2020-03-12 | Vertex Pharmaceuticals Incorporated | Co-crystals of modulators of cystic fibrosis transmembrane conductance regulator |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3525108A1 (de) | 1985-06-07 | 1986-12-11 | Bayer Ag, 5090 Leverkusen | Antibakteriell wirksame chinoloncarbonsaeureester |
| EP0876349B1 (en) * | 1995-10-19 | 2002-09-11 | Takeda Chemical Industries, Ltd. | Quinoline derivatives as gnrh antagonists |
| US6150522A (en) * | 1996-05-20 | 2000-11-21 | Merck & Co., Inc. | Antagonists of gonadotropin releasing hormone |
| CA2254974A1 (en) | 1996-05-20 | 1997-11-27 | Mark Goulet | Antagonists of gonadotropin releasing hormone |
-
2001
- 2001-02-21 DE DE2001108271 patent/DE10108271A1/de not_active Withdrawn
-
2002
- 2002-02-21 KR KR1020037010965A patent/KR100701806B1/ko not_active IP Right Cessation
- 2002-02-21 US US10/078,530 patent/US6790858B2/en not_active Expired - Fee Related
- 2002-02-21 UA UA2003087846A patent/UA73409C2/uk unknown
- 2002-02-21 AR ARP020100588A patent/AR035855A1/es unknown
-
2003
- 2003-08-19 ZA ZA200306429A patent/ZA200306429B/en unknown
-
2004
- 2004-07-23 US US10/896,961 patent/US7378522B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR20030082941A (ko) | 2003-10-23 |
| US7378522B2 (en) | 2008-05-27 |
| US20030105328A1 (en) | 2003-06-05 |
| KR100701806B1 (ko) | 2007-04-02 |
| US20050004127A1 (en) | 2005-01-06 |
| US6790858B2 (en) | 2004-09-14 |
| UA73409C2 (en) | 2005-07-15 |
| ZA200306429B (en) | 2004-02-11 |
| DE10108271A1 (de) | 2002-08-22 |
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