HRP20131073T1 - Organski spojevi - Google Patents
Organski spojevi Download PDFInfo
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- HRP20131073T1 HRP20131073T1 HRP20131073AT HRP20131073T HRP20131073T1 HR P20131073 T1 HRP20131073 T1 HR P20131073T1 HR P20131073A T HRP20131073A T HR P20131073AT HR P20131073 T HRP20131073 T HR P20131073T HR P20131073 T1 HRP20131073 T1 HR P20131073T1
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- 150000002894 organic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 24
- 238000000034 method Methods 0.000 claims 9
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical group C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 claims 6
- 201000001880 Sexual dysfunction Diseases 0.000 claims 6
- 231100000872 sexual dysfunction Toxicity 0.000 claims 6
- -1 4-(5-fluoropyrid-2-yl)benzyl Chemical group 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 claims 4
- 208000003532 hypothyroidism Diseases 0.000 claims 4
- 230000002989 hypothyroidism Effects 0.000 claims 4
- 230000009245 menopause Effects 0.000 claims 4
- 201000003631 narcolepsy Diseases 0.000 claims 4
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 3
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 3
- 208000018737 Parkinson disease Diseases 0.000 claims 3
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 3
- 208000010877 cognitive disease Diseases 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 229960003387 progesterone Drugs 0.000 claims 3
- 239000000186 progesterone Substances 0.000 claims 3
- 208000037853 Abnormal uterine bleeding Diseases 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 201000000736 Amenorrhea Diseases 0.000 claims 2
- 206010001928 Amenorrhoea Diseases 0.000 claims 2
- 201000005670 Anovulation Diseases 0.000 claims 2
- 206010002659 Anovulatory cycle Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 206010003805 Autism Diseases 0.000 claims 2
- 208000020706 Autistic disease Diseases 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- 102000004076 Dopamine D1 Receptors Human genes 0.000 claims 2
- 108090000511 Dopamine D1 Receptors Proteins 0.000 claims 2
- 101001117089 Drosophila melanogaster Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1 Proteins 0.000 claims 2
- 208000012661 Dyskinesia Diseases 0.000 claims 2
- 206010014733 Endometrial cancer Diseases 0.000 claims 2
- 206010014759 Endometrial neoplasm Diseases 0.000 claims 2
- 208000001914 Fragile X syndrome Diseases 0.000 claims 2
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 206010027339 Menstruation irregular Diseases 0.000 claims 2
- 208000016285 Movement disease Diseases 0.000 claims 2
- 208000001132 Osteoporosis Diseases 0.000 claims 2
- 208000005107 Premature Birth Diseases 0.000 claims 2
- 206010036590 Premature baby Diseases 0.000 claims 2
- 206010036618 Premenstrual syndrome Diseases 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
- 208000005793 Restless legs syndrome Diseases 0.000 claims 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 208000000323 Tourette Syndrome Diseases 0.000 claims 2
- 208000016620 Tourette disease Diseases 0.000 claims 2
- 206010044565 Tremor Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 201000010105 allergic rhinitis Diseases 0.000 claims 2
- 231100000540 amenorrhea Toxicity 0.000 claims 2
- 231100000552 anovulation Toxicity 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 230000001363 autoimmune Effects 0.000 claims 2
- 208000026106 cerebrovascular disease Diseases 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 206010013663 drug dependence Diseases 0.000 claims 2
- 230000002708 enhancing effect Effects 0.000 claims 2
- 239000000262 estrogen Substances 0.000 claims 2
- 229940011871 estrogen Drugs 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 206010020718 hyperplasia Diseases 0.000 claims 2
- 208000000509 infertility Diseases 0.000 claims 2
- 231100000535 infertility Toxicity 0.000 claims 2
- 230000036512 infertility Effects 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 230000037081 physical activity Effects 0.000 claims 2
- 210000002307 prostate Anatomy 0.000 claims 2
- 239000003368 psychostimulant agent Substances 0.000 claims 2
- 208000002815 pulmonary hypertension Diseases 0.000 claims 2
- 150000003839 salts Chemical group 0.000 claims 2
- 230000019491 signal transduction Effects 0.000 claims 2
- 230000007781 signaling event Effects 0.000 claims 2
- 208000019116 sleep disease Diseases 0.000 claims 2
- 208000020685 sleep-wake disease Diseases 0.000 claims 2
- 208000011117 substance-related disease Diseases 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- PROQIPRRNZUXQM-UHFFFAOYSA-N (16alpha,17betaOH)-Estra-1,3,5(10)-triene-3,16,17-triol Natural products OC1=CC=C2C3CCC(C)(C(C(O)C4)O)C4C3CCC2=C1 PROQIPRRNZUXQM-UHFFFAOYSA-N 0.000 claims 1
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims 1
- YFGHCGITMMYXAQ-UHFFFAOYSA-N 2-[(diphenylmethyl)sulfinyl]acetamide Chemical compound C=1C=CC=CC=1C(S(=O)CC(=O)N)C1=CC=CC=C1 YFGHCGITMMYXAQ-UHFFFAOYSA-N 0.000 claims 1
- SJZRECIVHVDYJC-UHFFFAOYSA-M 4-hydroxybutyrate Chemical compound OCCCC([O-])=O SJZRECIVHVDYJC-UHFFFAOYSA-M 0.000 claims 1
- 229910006124 SOCl2 Inorganic materials 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000002269 analeptic agent Substances 0.000 claims 1
- 239000000935 antidepressant agent Substances 0.000 claims 1
- 229940005513 antidepressants Drugs 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 229960005309 estradiol Drugs 0.000 claims 1
- 229930182833 estradiol Natural products 0.000 claims 1
- 150000002159 estradiols Chemical class 0.000 claims 1
- PROQIPRRNZUXQM-ZXXIGWHRSA-N estriol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H]([C@H](O)C4)O)[C@@H]4[C@@H]3CCC2=C1 PROQIPRRNZUXQM-ZXXIGWHRSA-N 0.000 claims 1
- 229960001348 estriol Drugs 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229960001165 modafinil Drugs 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 239000000583 progesterone congener Substances 0.000 claims 1
Classifications
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- 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
- C07D487/12—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 three hetero rings
- C07D487/14—Ortho-condensed systems
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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- 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
- C07D401/10—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 carbon chain containing aromatic rings
Claims (15)
1. Spoj formule Q
[image]
gdje
(i) -X-Y-Z se izabire između 4-(5-fluoropirid-2-il)benzil, 4-(6-fluoropirid-2-il)benzil, 4-(3-fluoropirid-2-il)benzil, 4-(4-fluoropirid-2-il)benzil;
(ii) R4 i R5 su nezavisno H, C1-6alkil ili aril po izboru supstituirani s jednim ili više halo, hidroksi ili C1-6alkoksi;
u slobodnom obliku ili obliku soli.
2. Spoj prema zahtjevu 1, gdje X-Y-Z je 4-(6-fluoropirid-2-il)benzil.
3. Spoj prema zahtjevu 1 ili zahtjevu 2, gdje R4 ili R5 je fenil po izboru supstituiran s jednim ili više halo, hidroksi ili C1-6alkoksi.
4. Spoj prema bilo kojem prethodnom zahtjevu, gdje R4 je H i R5 je fenil.
5. Spoj prema zahtjevu 1, gdje je taj spoj
[image]
6. Farmaceutski pripravak koji sadrži spoj prema bilo kojem od zahtjeva 1-5 u zajedničkoj smjesi s farmaceutski prihvatljivim punilom ili nosačem.
7. Spoj kako je definiran u bilo kojem od zahtjeva 1 do 5, u slobodnom obliku ili obliku soli, za uporabu kao farmaceutik.
8. Spoj kako je definiran u bilo kojem od zahtjeva 1 do 5 ili pripravak kako je definiran u zahtjevu 6 za uporabu u postupku liječenja bilo kojeg od sljedećih stanja: Parkinsonova bolest, nemirne noge, tremori, diskinezije, Huntingtonova bolest, Alzheimerova bolest i lijekovima inducirani poremećaji kretanja; depresija, poremećaj hiperaktivnosti i manjka pažnje, bipolarna bolest, anksioznost, poremećaj spavanja, narkolepsija, kognitivni poremećaj, demencija, Touretteov sindrom, autizam, sindrom fragilnog X, ustezanje psihostimulansa, i/ili ovisnost o drogama; cerebrovaskularna bolest, moždani udar, kongestivna bolest srca, hipertenzija, plućna hipertenzija, i/ili seksualna disfunkcija; astma, kronična opstruktivna plućna bolest, i/ili alergijski rinitis, kao i autoimune i upalne bolesti; i/ili seksualna disfunkcija u žena, amenoreja zbog tjelesne aktivnosti, anovulacija, menopauza, simptomi menopauze, hipotireoza, pre-menstrualni sindrom, preuranjeni porod, neplodnost, neredoviti menstrualni ciklusi, abnormalno uterino krvarenje, osteoporoza, multipla skleroza, povećanje prostate, rak prostate, hipotireoza, estrogenom inducirana hiperplazija ili karcinom endometrija; i/ili bilo koja bolest ili stanje naznačeni niskim razinama cAMP i/ili cGMP (ili inhibicijom cAMP i/ili cGMP signalnih putova) u stanicama koje eksprimiraju PDE1, i/ili smanjenom signalnom aktivnosti dopamin D1 receptora; i/ili bilo koja bolest ili stanje koji se mogu ublažiti tako da se pojača signal progesterona; koji obuhvaća primjenu učinkovite količine spoja prema bilo kojem od zahtjeva 1-5, ili farmaceutskog pripravka prema zahtjevu 6, bolesniku kojemu je to potrebno.
9. Spoj ili pripravak za uporabu u postupku prema zahtjevu 8, gdje je stanje:
Parkinsonova bolest;
kognitivni poremećaj;
narkolepsija; ili
seksualna disfunkcija u žena.
10. Spoj ili pripravak za uporabu u postupku prema zahtjevu 9, gdje je stanje narkolepsija i postupak dalje obuhvaća primjenu spoja ili spojeva izabranih između stimulansa središnjeg živčanog sustava, modafinila, antidepresiva i gama hidroksibutirata, bolesniku kojemu je to potrebno.
11. Spoj ili pripravak za uporabu u postupku prema zahtjevu 9, gdje je stanje seksualna disfunkcija u žena i postupak dalje obuhvaća primjenu spoja ili spojeva izabranih iz grupe koja obuhvaća estradiol, estriol, estere estradiola, progesteron i progestine bolesniku kojemu je to potrebno.
12. Postupak proizvodnje spoja prema bilo kojem od zahtjeva 1 do 5, obuhvaća reakciju
a) (6aR,9aS)-3-(fenilamino)-5-6a,7,8,9,9a-heksahidro-5-metil-ciklopent[4,5]imidazo[1,2-a]pirazolo[4,3-e]pirimidin-4(2H)-ona Formule QK:
[image]
gdje R1 je metil; i R4 i R5 su kako je definirano u bilo kojem od zahtjeva 1, 3 i 4, sa
b) spojem formule Z-Y-X-L gdje je L odlazeća skupina i X, Y i Z su kako je definirano u zahtjevu 1 ili zahtjevu 2,
te izolaciju spoja prema bilo kojem od zahtjeva 1 do 5 dobivenog na ovaj način.
13. Postupak proizvodnje spoja prema bilo kojem od zahtjeva 1 do 5, koji obuhvaća ciklizaciju spoja Formule QV
[image]
gdje R1 je metil; i R4 i R5 su kako je definirano u bilo kojem od zahtjeva 1, 3 i 4 i -X-Y-Z je kako je definirano u zahtjevu 1 ili zahtjevu 2, sa sredstvom za dehidraciju/halogeniranje.
14. Postupak prema zahtjevu 13, gdje je to sredstvo SOCl2.
15. Uporaba spoja prema bilo kojem od zahtjeva 1-5 ili farmaceutskog pripravka prema zahtjevu 6 za proizvodnju lijeka za liječenje ili prevenciju sljedećih bolesti: Parkinsonova bolest, nemirne noge, tremori, diskinezije, Huntingtonova bolest, Alzheimerova bolest i lijekovima inducirani poremećaji kretanja; depresija, poremećaj manjka pažnje, poremećaj hiperaktivnosti i manjka pažnje, bipolarna bolest, anksioznost, poremećaj spavanja, narkolepsija, kognitivni poremećaj, demencija, Touretteov sindrom, autizam, sindrom fragilnog X, ustezanje psihostimulansa, i/ili ovisnost o drogama; cerebrovaskularna bolest, moždani udar, kongestivna bolest srca, hipertenzija, plućna hipertenzija, i/ili seksualna disfunkcija; astma, kronična opstruktivna plućna bolest, i/ili alergijski rinitis, kao i autoimune i upalne bolesti; i/ili seksualna disfunkcija u žena, amenoreja zbog tjelesne aktivnosti, anovulacija, menopauza, simptomi menopauze, hipotireoza, pre-menstrualni sindrom, preuranjeni porod, neplodnost, neredoviti menstrualni ciklusi, abnormalno uterino krvarenje, osteoporoza, multipla skleroza, povećanje prostate, rak prostate, hipotireoza, estrogenom inducirana hiperplazija ili karcinom endometrija; i/ili bilo koja bolest ili stanje naznačeni niskim razinama cAMP i/ili cGMP (ili inhibicijom cAMP i/ili cGMP signalnih putova) u stanicama koje eksprimiraju PDE1, i/ili smanjenom signalnom aktivnosti dopamin D1 receptora; i/ili bilo koja bolest ili stanje koji se mogu ublažiti tako da se pojača signal progesterona; koja obuhvaća primjenu učinkovite količine spoja prema bilo kojem od zahtjeva 1-5, ili farmaceutskog pripravka prema zahtjevu 6, bolesniku kojemu je to potrebno.
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2008
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