| Imidazo[1,2-b]pyridazine compound -> Monitor Keywords |
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Imidazo[1,2-b]pyridazine compoundRelated Patent Categories: Drug, Bio-affecting And Body Treating Compositions, Designated Organic Active Ingredient Containing (doai), Heterocyclic Carbon Compounds Containing A Hetero Ring Having Chalcogen (i.e., O,s,se Or Te) Or Nitrogen As The Only Ring Hetero Atoms Doai, Hetero Ring Is Six-membered Consisting Of Three Nitrogens And Three Carbon Atoms, Asymmetrical (e.g., 1,2,4-triazine, Etc.), Polycyclo Ring System Having The Hetero Ring As One Of The CyclosImidazo[1,2-b]pyridazine compound description/claimsThe Patent Description & Claims data below is from USPTO Patent Application 20060211696, Imidazo[1,2-b]pyridazine compound. Brief Patent Description - Full Patent Description - Patent Application Claims
[0001] This application is a Divisional of co-pending application Ser. No. 10/451,741 filed on Jun. 25, 2003 and for which priority is claimed under 35 U.S.C. .sctn.120. application Ser. No. 10/451,741 is the national phase of PCT International Application No. PCT/JP02/01098 filed on Feb. 8, 2002 under 35 U.S.C. .sctn.371. The entire contents of each of the above-identified applications are hereby incorporated by reference. FIELD OF THE INVENTION [0002] The present invention relates to a novel compound having corticotropin-releasing-factor receptor antagonistic activity, a salt thereof and a hydrate of them, a process for preparing its and its medical use. PRIOR ART [0003] Corticotropin-releasing-factor (hereinafter, referred to as "CRF") is a neuropeptide comprising 41 amino acids, and isolated from sheep hypothalamus (Science, 213, 1394 (1981)) and, then, its presence was confirmed in a rat (Proc. Natl. Acad. Sci. USA, 80, 4851 (1983)) and a human being (EMBO J. 5, 775 (1983)). CRF is the most abundant in pituitary gland and hypothalamus and is widely distributed in a brain such as cerebral cortex, cerebellum and the like. In addition, in a peripheral tissue, CRF is confirmed to be present in placenta, adrenal gland, lung, lever, pancreas and digestive tract (J. Clin. Endocrinol. Metab., 65, 176 (1987), J. Clin. Endocrinol. Metab., 67, 768 (1988), Regul. Pept., 18, 173 (1987), peptides, 5 (Suppl. 1), 71 (1984)). Two subtypes CRF1 and CRF2 are present in a CRF receptor, and a CRF1 receptor is reported to be distributed at a large amount in cerebral cortex, cerebellum, olfactory bulb, pituitary gland, almond nucleus and the like. Recently, two subtypes CRF2.alpha. and CRF2.beta. were confirmed to be present in a CRF2 receptor, and it was found that a CRF2.alpha. receptor is distributed in hypothalamus, septal area and choroid plexus at a large amount and a CRF2.beta. is distributed in a peripheral tissue such as skeletal muscle and in a cerebrovascular part in central tissue (J. Neuroscience, 15 (10) 6340 (1995); Endocrinology, 137, 72 (1996); BBA, 1352, 129 (1997)). Since each receptor is distributed differently, it is suggested that its role is also different. CRF is produced in and secrete from hypothalamus and promotes the release of adrenocorticotropic hormone (ACTH) by stress (Recent Prog. Horm. Res., 39, 245(1983)). CRF serves as a neurotransmitter or a neuromodulator also in a brain and integrates electrophysiology to stress, autonomic nerve and action, in addition to a role to incretion (Brain Res. Rev., 15, 71, (1990); Pharmacol. Rev., 43, 425 (1991)). [0004] Currently, CRF is thought to be involved in a variety of diseases and there are reports as follows: [0005] CRF in a cerebrospinal liquid in a depression patient is at a higher value as compared with a healthy man (Am. J. Psychiatry, 144 (7), 873 (1987)). A CRF-mRNA level in hypothalamus in a depression patient is a higher value as compared with a healthy man (Am. J. Psychiatry, 152, 1372 (1995)). A CRF receptor is decreased in a cerebral cortex of a person who commits suicide (Arch. Gen. Psychiatry, 45, 577 (1988)). A rise of ACTH in a plasma is small in a depression patient upon administration of CRF (N. Engl. J. Med., 314,1329 (1986)). CRF in a cerebrospinal liquid of a certain anxiety patient such as compulsion disorder, posttraumatic stress disorder, teulett syndrome etc. is a higher value as compared with a healthy man (Arch. Gen. Psychiatry, 51, 794 (1994); Am. J. Psychiatry, 154, 624 (1997); Biol. Psychiatry, 39, 776 (1996)). A rise of ACTH in a plasma is small in a panic disorder patient upon administration of a CRF (Am. J. Psychiatry, 143, 896 (1986)). An anxiety behavior is recognized when CRF is administered in a brain of an experimental animal (Brain Res., 574, 70 (1992); J. Neurosci., 10 (1), 176 (1992)). In addition, many anxiety behavior are recognized in a CRF overexpressing mouse as compared with a normal animal (J. Neurosci., 14 (5), 2579 (1994)). CRF ceruleus is decreased by administration of an anti-anxiety agent (J. Pharmaco. Exp. Ther., 258, 349 (1991)). In addition, .alpha.-helical CRF (9-41) of a peptidic CRF antagonist exerts an anti-anxiety behavior in an animal model (Brain Res., 509, 80 (1990); Regulatory Peptize, 18, 37 (1987); J. Neurosci., 14 (5), 2579 (1994)). .alpha.-Helical CRF (9-41) of a peptidic CRF antagonist inhibits an abnormal behavior due to abstinence of dependency drug such as alcohol and cocaine (Psychopharmacology, 103, 227 (1991)). CRF suppresses a sexual behavior of a rat (Nature, 305, 232 (1983)). CRF is thought to be involved in sleep disorder because it reduces rat's sleep (Pharmacol. Biochem. Behav., 26, 699 (1987)). .alpha.-Helical CRF (9-41) of a peptidic CRF antagonist inhibits disorder of a brain and brain wave abnormality due to brain ischemia and activation of NMDA receptor (Brain Res., 545, 339 (1991), Brain Res. 656, 405 (1994)). CRF awakens a brain wave and induces convulsion (Brain Res., 278, 332 (1983)). CRF in a cerebrospinal liquid of a schizophrenia patient is a higher value as compared with a healthy man (Am. J. Psychiatry, 144(7), 873 (1987)). CRF in a cerebral cortex in an Alzheimer's disease, Parkinson's disease or progressive supranuclear palsy is reduced (Neurology, 37, 905 (1987)). CRF in a Huntington disease ganglion is reduced (Brain Res., 437, 355 (1987), Neurology, 37, 905 (1987)). In addition, it has been found that administration of CRF in a rat enhances learning and memory (Nature, 378, 384 (1995); Neuroendocrinology, 57, 1071 (1993)). CRF in a cerebrospinal liquid in an amyotrophic lateral sclerosis patient. In a CRF overexpressing mouse, oversecretion of ACTH and adrenal gland steroid hormone occurs and abnormality similar to Cushing syndrome such as muscular atrophy, alopecia and infertility (Endocrinology, 130(6), 3378 (1992)). CRF in a cerebrospinal liquid in an anorexia nervosa patient is a higher value as compared with a healthy man, and a rise of ACTH in a plasma is small in an anorexia nervosa upon administration of CRF (J. Clin. Endocrinol. Metab., 62, 319 (1986)). CRF suppresses eating in an experimental animal (Neuropharmacology, 22 (3A), 337 (1983)). In addition, .alpha.-helical CRF (9-41) of a peptidic CRF antagonist improved decrease in eating in an animal model due to stress load (Brain Res. Bull., 17 (3), 285 (1986)). CRF suppressed weight gain in a hereditary obesity animal (Physiol. Behav., 45, 565 (1989)). It is suggested that the lowness of a CRF value and obesity syndrome are related (Endocrinology, 130, 1931 (1992)). It is suggested that eating inhibition and weight loss action of a serotonine reuptake inhibiting agent is via release of CRF (Pharmacol. Rev., 43, 425 (1991)). CRF acts on centralness and peripherallness, weakens constriction of a stomach and reduces stomach excretion ability (Regulatory Peptides, 21, 173 (1983); Am. J. Physiol., 253, G241 (1987)). In addition, .alpha.-helical CRF (9-41) of a peptidic CRF antagonist has the recovery action on the functional decrease of stomach due to abdominal operation (Am. J. Physiol., 262, G616 (1992)). CRF promotes secretion of bicarbonate ions in stomach, decreases gastric acid secretion, and at the same time, inhibits cold constraint stress ulcer (Am. J. Physiol., 258, G152 (1990)). In addition, ulcer is increased in a non-constraint animal by CRF administration (Life Sci., 45, 907 (1989)). CRF suppresses small intestine transport, promotes large intestine transport and induces defecation. In addition, .alpha.-helical CRF (9-41) of a peptidic CRF antagonist has the inhibitory action on decrease in gastric acid secretion, decrease in stomach excretion, decrease in small intestine transport and asthenia in large intestine (Gastroenterology, 95,1510(1988)). 26) In a healthy man, mental stress increases a gas and bellyache due to anxiety and gastrectasis and CRF reduces a threshold of uncomfort (Gastroenterol., 109, 1772 (1995); Neurogastroenterol. Mot., 8, 9 (1996)). In an irritable bowel syndrome patient, large intestine movement is excessively exasperated by administration of CRF as compared with a healthy man (Gut., 42, 845 (1998)). Administration of CRF increases blood pressure, heart rate and body temperature. In addition, .alpha.-helical CRF (9-41) of a peptidic CRF antagonist inhibits elevation of blood pressure, heart rate and body temperature (J. Physiol., 460, 221 (1993)). In an inflammatory part of an experimental animal and a joint liquid of a rheumatoid arthritis patient, production of CRF is locally increased (Science, 254, 421(1991); J. Clin. Invest., 90, 2555 (1992); J. Immunol., 151, 1587 (1993)). CRF induces degranulation of a mast cell and exasperates vessel permeability (Endocrinology, 139(1), 403 (1998); J. Parmacol. Exp. Ther., 288 3), 1349 (1999)). Also in an autoimmune thyroiditis patient, CRF is detected (Am. J. Pathol., 145, 1159 (1994)). When CRF is administered to an experimental autoimmune cerebrospinal meningitis rat, progression of symptom of palsy and the like was remarkably inhibited (J. Immunol., 158, 5751 (1997)). In a system for culturing pituitary gland adenocarcinoma of an acromegaly patient, urocortin (analogue of CRF) increased secretion of a growth hormone (Endocri, J., 44, 627 (1997)). In addition, CRF stimulates secretion of cytokin such as interleukin 1 and interleukin2 (J. Neuroimmunol., 23,256(1989); Neurosci. Lett., 120, 151(1990)). Activity of natural killer cell and increase of T lymphocyte are decreased by administration of CRF and load of stress. .alpha.-Helical CRF (9-41) of a peptidic CRF antagonist improves decrease in the function of immune cells due to administration of CRF and stress load (Endocrinology, 128 (3), 1329 (1991)). Breathing is remarkably increased by administration of CRF (Eur. J. Pharmacol., 182, 405 (1990)). In an advanced aged patient equipped with a long term artificial inhaler, animus of breathing and insomnia were recognized by administration of CRF (Acta Endcrinol. Copenh., 127, 200 (1992)). [0006] From the above study reports, a CRF antagonist can be expected to exert the excellent effects in treating or preventing depression and depressive symptom including great depression, monostotic depression, recurrent depression, infant tyrannism by depression and postpartum depression, mania, anxiety, generalized anxiety disorder, panic disorder, phobia, compulsive disorder, posttraumatic stress disorder, Tourette syndrome, autism, emotional disorder, sentimental disorder, bipolar disorder, cyclothymia, schizophrenia, Alzheimer's disease, Alzheimer-type senile dementia, neurodegenerative disease such as Parkinson's disease and Huntington's disease, multi-infarct dementia, senile dementia, neurotic anorexia, appetite asthenia and other diet disorder, obesity, diabetes, alcohol dependence, pharmacophilia to cocaine, heroin, benzodiazepine etc., drug or alcohol withdrawal, sleep disorder, insomnia, migraine, stress headache, myotonic headache, ischemic neuropathy, excitation toxic neuropathy, cerebral apoplexy, progressive supranuclear palsy, amyotrophic lateral sclerosis, multiple sclerosis, muscular convulsion, chronic fatigue syndrome, mental social growth failure, epilepsy, head trauma, spinal trauma, graphospasm, spasmodic torticollis, muscular convulsion, neck-shoulder-arm syndrome, primary glaucoma, Meniere syndrome, autonomic imbalance, alopecia, neurosis including cardioneurosis, intestinal neurosis and bladder neurosis, peptic ulcer, irritable bowel syndrome, ulcerative colitis, Crohn's disease, diarrhea, coprostasis, postoperational ileus, gastrointestinal function abnormality associated with stress and neural vomiting, hypertension, cardiovascular disorder including neural angina, tachycardia, congestive cardioplegia, hyperpnea syndrome, bronchial asthma, apnea syndrome, infant sudden death syndrome, inflammatory disorder (for example, rheumatoid arthritis, bone arthritis, lumbago etc.), pain, allergic disease (for example, atopic dermatis, eczema, urticaria, psoriasis etc.), impotence, climacteric disorder, fertilization disorder, infertility, cancer, immune function abnormality upon infection with HIV, immune function abnormality by stress, hemorrhagic stress, Cushing syndrome, thyroid function disorder, encephalomyelitis, acromegaly, incontinence, osteoporosis etc. There is a report on a CRF antagonist, for example, a peptide-type CRF receptor antagonist in which a part of an amino acid sequence of a human being or other mammal is altered or deleted, and it is reported that the antagonist shows the ACTH release inhibitory action and anti-anxiety action of the antagonist (Science, 224, 889 (1984), J. Pharmacol. Exp. Ther., 269, 564 (1994), Brain Research Reviews, 15, 71 (1990)). However, it must be said that, from a viewpoint of pharmacokinetics such as the chemical stability in vivo, the bioavailability and the transferability to brain, the utility value thereof as a medicament is low. [0007] On the other hand, regarding a non-peptide type CRF antagonist, there is the following report: [0008] 1) a compound represented by the formula: (wherein R.sup.1 represents NR.sup.4R.sup.5 etc.; R.sup.2represents a C.sub.1-6 alkyl group etc.; R.sup.3 represents a C.sub.1-6 alkyl group etc.; R.sup.4 represents a C.sub.1-6 alkyl group etc.; R.sup.5 represents a C.sub.1-6 alkyl group etc.; and Ar represents phenyl etc.), a stereoisomer thereof, or pharmaceutically acceptable acid addition salts thereof (WO97/29109); [0009] 2) a compound represented by the formula: (wherein a broken line represents a single or double bond; A represents CR.sup.7 etc.; B represents NR.sup.1R.sup.2 etc.; J and K are the same as or different from each other and each represents nitrogen atom etc.; D and E are the same as or different from each other and each represents nitrogen atom etc.; G denotes nitrogen atom etc.; R.sup.1 represents a C.sub.1-6 alkyl group etc.; R.sup.2 represents a C.sub.1-C.sub.12 alkyl group etc.; and R.sup.7 represents hydrogen atom etc.) or a pharmacologically acceptable salt thereof (WO98/08847); [0010] 3) an anilinopyrimidine compound described in WO95/10506, a pyrazolopyrimidine compound described in WO95/34563, a pyrazole compound described in WO94/13661, a pyrazole and pyrazolopyrimidine compound described in WO94/13643, aminopyrazole described in WO94/18644, a pyrazolopyrimidine compound described in WO94/13677, a pyrrolopyrimidine compound described in WO94/13676, a thiazole compound described in EP-659747, EP-611766, an anilinopyrimidine compound described in J. Med. Chem., 39, 4358 (1996), an anilinotriazine compound described in ibid. 39, 3454 (1996), a thienopyrimidine compound described in WO97/29110 and the like; and [0011] 4) as an imidazo[1,2-a]pyrazine compound, there is, for example, a compound described in EP0068378 and, as an imidazo[1,2-b]pyridazine compound, there is, for example, a compound described in EP0353902. [0012] As described above, there is desired the provision of a CRF receptor antagonist which is useful as a medicament. However, a medicament which shows the excellent CRF receptor antagonism, and satisfies the pharmacological activity, the dose, the safety etc. as a medicament and effectively acts clinically has not been found. That is, an object of the present invention is to search and find such the excellent CRF receptor antagonist. DISCLOSURE OF THE INVENTION [0013] In view of the above-mentioned circumstances, the present inventors studied intensively and, as a result, they have succeeded in synthesizing a novel compound (hereinafter, referred to as "the compound (I)" in some cases) represented by the following formula: (wherein R.sup.1 denotes a hydrogen atom, a halogen atom, a nitro group, a cyano group, a C.sub.1-6 alkyl group, a C.sub.2-8 alkenyl group, a C.sub.2-8 alkynyl group, a C.sub.3-8 cycloalkyl group, a C.sub.3-8 cycloalkenyl group, a C.sub.1-6 alkoxy group, a C.sub.2-6 alkenyloxy group, or a group represented by --NR.sup.1aR.sup.1b (R.sup.1a and R.sup.1b are the same as or different from each other and each denotes a hydrogen atom, a C.sub.1-6 alkyl group, a C.sub.2-6 alkenyl group, a C.sub.2-6 alkynyl group, a C.sub.1-6 alkylsulfinyl group, a C.sub.1-6 alkylsulfonyl group or a C.sub.1-7 aliphatic acyl group), --CO--NR.sup.1aR.sup.1b (R.sup.1a and R.sup.1b have the same meanings as defined above, respectively), --CO--A.sup.1 (A.sup.1 denotes a C.sub.1-6 alkyl group, a C.sub.2-8 alkenyl group or a C.sub.2-8 alkynyl group), -G.sup.1-A.sup.2 (G.sup.1 denotes --O--CO--, S, SO or SO.sub.2; and A.sup.2 denotes a C.sub.1-6 alkyl group or a C.sub.2-6 alkenyl group) or --SO.sub.2--NR.sup.1aR.sup.1b (R.sup.1a and R.sup.1b have the same meanings as defined above, respectively), and further, the R.sup.1 may be substituted with at least one group selected from a halogen atom, a cyano group, a C.sub.1-6 alkyl group, a C.sub.2-8 alkenyl group, a C.sub.2-8 alkynyl group, a C.sub.1-6 alkoxy group, a C.sub.1-6 alkenyloxy group, a C.sub.1-6 alkylthio group and a C.sub.2-6 alkenylthio group; [0014] R.sup.2 denotes: [0015] (a) a halogen atom, a cyano group, a nitro group, a C.sub.1-10 alkyl group, a C.sub.2-10 alkenyl group, a C.sub.2-10 alkynyl group, a C.sub.2-8 cycloalkyl group, a C.sub.3-8 cycloalkenyl group, a C.sub.3-8 cycloalkyl C.sub.1-6 alkyl group, a C.sub.3-8 cycloalkyl C.sub.2-6alkenyl group, a C.sub.1-10alkoxy group, a C.sub.2-6 alkenyloxy group, a C.sub.1-10 alkoxy C.sub.1-10 alkyl group, a C.sub.1-6 alkoxy C.sub.2-8 alkenyl group, a C.sub.2-6 alkenyloxy C.sub.1-6 alkyl group, a C.sub.2-6 alkenyloxy C.sub.2-6 alkenyl group, a group represented by --NR.sup.2aR.sup.2b (R.sup.2a and R.sup.2b are independent of each other and each denotes a hydrogen atom, a C.sub.1-8 alkyl group, a C.sub.2-8 alkenyl group, a C.sub.2-6 alkynyl group, a C.sub.1-6 hydroxyalkyl group, a C.sub.1-6alkyl group substituted with a 5- to 14-membered non-aromatic heterocyclic group, a C.sub.1-6 alkylthio group, a C.sub.1-6 alkylsulfinyl group, a C.sub.1-6 alkylsulfonyl group, a C.sub.1-6 alkoxy C.sub.1-6 alkyl group, a C.sub.1-6alkylthio C.sub.1-6 alkyl group, an aminocarbonyl C.sub.1-6 alkyl group, a heteroarylcarbonyl group, a C.sub.3-8 cycloalkyl group, a C.sub.3-8 cycloalkyl C.sub.1-6 alkyl group, a heteroaryl C.sub.1-6 alkyl group, an aryl C.sub.1-6 alkyl group, an aryl group, a 5- to 14-membered heterocyclic group, a C.sub.1-6 alkoxycarbonyl group or a C.sub.2-6 alkenyloxycarbonyl group), --CO--NR.sup.2aR.sup.2b (R.sup.2a and R.sup.2b have the same meanings as defined above, respectively), --CO-A.sup.3 (A.sup.3 denotes a hydrogen atom, a hydroxyl group, a C.sub.1-6alkyl group, a C.sub.2-8alkenyl group, a C.sub.2-8 alkynyl group, a C.sub.1-6 alkoxy group, a C.sub.2-8 alkenyloxy group, an aryl group or a heteroaryl group), --O--C(O)-A.sup.4 (A.sup.4 denotes a C.sub.1-6 alkyl group, a C.sub.2-8 alkenyl group or a C.sub.2-8 alkynyl group) or -G.sup.2-A.sup.5 (G.sup.2 denotes S, SO or SO.sub.2; and A.sup.5 denotes a C.sub.1-6 alkyl group or a C.sub.2-6 alkenyl group), or a 5- to 14-membered non-aromatic heterocyclic group, or [0016] (b) may be bound together with R.sup.1 to form a cycle, and further, [0017] in the case of (a) or (b), R.sup.2 may be substituted with at least one group selected from a halogen atom, a hydroxyl group, a cyano group, a C.sub.1-6 alkyl group, a C.sub.2-6 alkenyl group, a C.sub.2-6 alkynyl group, a C.sub.2-8 cycloalkyl group, a C.sub.3-8 cycloalkenyl group, a C.sub.1-6 alkoxy group, a C.sub.2-6 alkenyloxy group, a C.sub.1-6 alkylthio group, a C.sub.2-6 alkenylthio group, --NR.sup.2aR.sup.2b (R.sup.2a and R.sup.2b have the same meanings as defined above, respectively), an aryl group and a heteroaryl group; [0018] R.sup.3 denotes a C.sub.6-14 aromatic hydrocarbon cyclic group or a 5- to 14-membered aromatic heterocyclic group, each of which may have a substituent; and [0019] X, Y and Z are independent of each other and each denotes (a) N or (b) CR.sup.4 (wherein R.sup.4 (aa) denotes a hydrogen atom, a halogen atom, a cyano group, a nitro group, an optionally halogenated C.sub.1-6 alkyl group, a C.sub.2-6 alkenyl group, a C.sub.2-6 alkynyl group, a C.sub.3-8 cycloalkyl group, a C.sub.3-8 cycloalkenyl group, a C.sub.1-6 alkoxy group, a C.sub.2-6 alkenyloxy group, --NR.sup.4aR.sup.4b (wherein R.sup.4a and R.sup.4b are independent of each other and each denotes a hydrogen atom, a C.sub.1-8 alkyl group, a C.sub.2-8 alkenyl group, a C.sub.2-6 alkynyl group, a C.sub.1-6 alkylthio group, a C.sub.1-6 alkylsulfinyl group, a C.sub.1-6 alkylsulfonyl group, a C.sub.1-6 alkoxy C.sub.1-6 alkyl group, a C.sub.3-8 cycloalkyl group, a C.sub.3-8 cycloalkyl C.sub.1-6 alkyl group, a heteroaryl C.sub.1-6 alkyl group, an aryl C.sub.1-6 alkyl group, an aryl group, a 5- to 14-membered heterocyclic group, a C.sub.1-6 alkoxycarbonyl group or a C.sub.2-6 alkenyloxycarbonyl group) or -G.sup.3-A.sup.6 (wherein G.sup.3 denotes S, SO or SO.sub.2; A.sup.6 denotes a C.sub.1-6 alkyl group or a C.sub.2-6 alkenyl group), or (bb) R.sup.4s, or R.sup.2 and R.sup.4 may be bound together to form a ring); in this case, at least two of X, Y and Z denote CR.sup.4 (R.sup.4 has the same meaning as defined above), [0020] provided that, in the above definition, compounds in the following cases (1) to (4) are excluded: [0021] (1) the case where R.sup.1 and R.sup.2 are a methyl group, X, Y and Z are CH, and R.sup.3 is a 2,4-dichlorophenyl group, Continue reading about Imidazo[1,2-b]pyridazine compound... 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