HRP20151078T1 - Pirazoli kao 11-beta-hsd-1 - Google Patents
Pirazoli kao 11-beta-hsd-1 Download PDFInfo
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- HRP20151078T1 HRP20151078T1 HRP20151078TT HRP20151078T HRP20151078T1 HR P20151078 T1 HRP20151078 T1 HR P20151078T1 HR P20151078T T HRP20151078T T HR P20151078TT HR P20151078 T HRP20151078 T HR P20151078T HR P20151078 T1 HRP20151078 T1 HR P20151078T1
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- Prior art keywords
- carboxylic acid
- hydroxy
- pyrazole
- tert
- butyl
- Prior art date
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- 150000003217 pyrazoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 27
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 12
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 8
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 claims 4
- CWLUFVAFWWNXJZ-UHFFFAOYSA-N 1-hydroxypyrrolidine Chemical compound ON1CCCC1 CWLUFVAFWWNXJZ-UHFFFAOYSA-N 0.000 claims 4
- WNMQSIGDRWCJMO-UHFFFAOYSA-N 1-tert-butylpyrrolidine Chemical compound CC(C)(C)N1CCCC1 WNMQSIGDRWCJMO-UHFFFAOYSA-N 0.000 claims 4
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 claims 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 4
- 229910052736 halogen Chemical group 0.000 claims 4
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical compound ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 claims 4
- RJUAEBLXGFKZMS-UHFFFAOYSA-N piperidin-1-ylmethanol Chemical compound OCN1CCCCC1 RJUAEBLXGFKZMS-UHFFFAOYSA-N 0.000 claims 4
- 150000003852 triazoles Chemical class 0.000 claims 4
- -1 -C(CH3)2CH2OH Chemical group 0.000 claims 3
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 3
- 208000008589 Obesity Diseases 0.000 claims 3
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 206010012601 diabetes mellitus Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 150000002367 halogens Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 235000020824 obesity Nutrition 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 3
- RUBHMIRCYQGFQG-UHFFFAOYSA-N 1-cyclopropyl-n-(5-hydroxy-2-adamantyl)-5-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C1C(O)(CC2C3)CC3CC1C2NC(=O)C(=C1C(F)(F)F)C=NN1C1CC1 RUBHMIRCYQGFQG-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- ZRBZITBEXRKYHA-UHFFFAOYSA-N n-(2-adamantyl)-1-methyl-5-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound CN1N=CC(C(=O)NC2C3CC4CC(C3)CC2C4)=C1C(F)(F)F ZRBZITBEXRKYHA-UHFFFAOYSA-N 0.000 claims 2
- PBICESADEROPRB-UHFFFAOYSA-N n-(2-adamantyl)-1-methyl-5-pyrazol-1-ylpyrazole-4-carboxamide Chemical compound CN1N=CC(C(=O)NC2C3CC4CC(C3)CC2C4)=C1N1C=CC=N1 PBICESADEROPRB-UHFFFAOYSA-N 0.000 claims 2
- QNFMCMRZKCCDQI-UHFFFAOYSA-N n-(2-adamantyl)-1-tert-butyl-5-pyrazol-1-ylpyrazole-4-carboxamide Chemical compound CC(C)(C)N1N=CC(C(=O)NC2C3CC4CC(C3)CC2C4)=C1N1C=CC=N1 QNFMCMRZKCCDQI-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- ZLXTYRQSQMYVAK-UHFFFAOYSA-N n-(2-adamantyl)-1-cyclopropyl-5-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound FC(F)(F)C1=C(C(=O)NC2C3CC4CC(C3)CC2C4)C=NN1C1CC1 ZLXTYRQSQMYVAK-UHFFFAOYSA-N 0.000 claims 1
- QNWGNWHWKKKLBB-UHFFFAOYSA-N n-(2-adamantyl)-1-methyl-5-(1,2,4-triazol-1-yl)pyrazole-4-carboxamide Chemical compound CN1N=CC(C(=O)NC2C3CC4CC(C3)CC2C4)=C1N1C=NC=N1 QNWGNWHWKKKLBB-UHFFFAOYSA-N 0.000 claims 1
- QRPFPZTWMVXVIA-UHFFFAOYSA-N n-(2-adamantyl)-1-methyl-5-piperidin-1-ylpyrazole-4-carboxamide Chemical compound CN1N=CC(C(=O)NC2C3CC4CC(C3)CC2C4)=C1N1CCCCC1 QRPFPZTWMVXVIA-UHFFFAOYSA-N 0.000 claims 1
- ZYYDXDKIGCJUKO-UHFFFAOYSA-N n-(2-adamantyl)-1-methyl-5-pyrrolidin-1-ylpyrazole-4-carboxamide Chemical compound CN1N=CC(C(=O)NC2C3CC4CC(C3)CC2C4)=C1N1CCCC1 ZYYDXDKIGCJUKO-UHFFFAOYSA-N 0.000 claims 1
- HWNLZFKDLYDDDC-UHFFFAOYSA-N n-(2-adamantyl)-1-methyl-5-thiomorpholin-4-ylpyrazole-4-carboxamide Chemical compound CN1N=CC(C(=O)NC2C3CC4CC(C3)CC2C4)=C1N1CCSCC1 HWNLZFKDLYDDDC-UHFFFAOYSA-N 0.000 claims 1
- NRYKAZYQBHDWPZ-UHFFFAOYSA-N n-(2-adamantyl)-1-tert-butyl-5-(3-hydroxypyrrolidin-1-yl)pyrazole-4-carboxamide Chemical compound CC(C)(C)N1N=CC(C(=O)NC2C3CC4CC(C3)CC2C4)=C1N1CCC(O)C1 NRYKAZYQBHDWPZ-UHFFFAOYSA-N 0.000 claims 1
- NRJRWRYUCCMFGS-UHFFFAOYSA-N n-(2-adamantyl)-1-tert-butyl-5-(4-hydroxypiperidin-1-yl)pyrazole-4-carboxamide Chemical compound CC(C)(C)N1N=CC(C(=O)NC2C3CC4CC(C3)CC2C4)=C1N1CCC(O)CC1 NRJRWRYUCCMFGS-UHFFFAOYSA-N 0.000 claims 1
- NKCLVSRXBXBEGX-UHFFFAOYSA-N n-(2-adamantyl)-1-tert-butyl-5-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound CC(C)(C)N1N=CC(C(=O)NC2C3CC4CC(C3)CC2C4)=C1C(F)(F)F NKCLVSRXBXBEGX-UHFFFAOYSA-N 0.000 claims 1
- VLWSIQBJHKARQX-UHFFFAOYSA-N n-(2-adamantyl)-1-tert-butyl-5-piperidin-1-ylpyrazole-4-carboxamide Chemical compound CC(C)(C)N1N=CC(C(=O)NC2C3CC4CC(C3)CC2C4)=C1N1CCCCC1 VLWSIQBJHKARQX-UHFFFAOYSA-N 0.000 claims 1
- FFYOFTXJMACLOS-UHFFFAOYSA-N n-(2-adamantyl)-1-tert-butyl-5-pyrrolidin-1-ylpyrazole-4-carboxamide Chemical compound CC(C)(C)N1N=CC(C(=O)NC2C3CC4CC(C3)CC2C4)=C1N1CCCC1 FFYOFTXJMACLOS-UHFFFAOYSA-N 0.000 claims 1
- SNYBKZDXTKZFBG-UHFFFAOYSA-N n-(2-adamantyl)-5-(3-hydroxypyrrolidin-1-yl)-1-methylpyrazole-4-carboxamide Chemical compound CN1N=CC(C(=O)NC2C3CC4CC(C3)CC2C4)=C1N1CCC(O)C1 SNYBKZDXTKZFBG-UHFFFAOYSA-N 0.000 claims 1
- YRZBCRJWOKGAKB-UHFFFAOYSA-N n-(2-adamantyl)-5-(4-benzylpiperazin-1-yl)-1-methylpyrazole-4-carboxamide Chemical compound CN1N=CC(C(=O)NC2C3CC4CC(C3)CC2C4)=C1N(CC1)CCN1CC1=CC=CC=C1 YRZBCRJWOKGAKB-UHFFFAOYSA-N 0.000 claims 1
- DSYNXHHCCPXFHI-UHFFFAOYSA-N n-(2-adamantyl)-5-(4-hydroxypiperidin-1-yl)-1-methylpyrazole-4-carboxamide Chemical compound CN1N=CC(C(=O)NC2C3CC4CC(C3)CC2C4)=C1N1CCC(O)CC1 DSYNXHHCCPXFHI-UHFFFAOYSA-N 0.000 claims 1
- LVXCVDKHYCXECN-UHFFFAOYSA-N n-(2-adamantyl)-5-[4-(hydroxymethyl)piperidin-1-yl]-1-methylpyrazole-4-carboxamide Chemical compound CN1N=CC(C(=O)NC2C3CC4CC(C3)CC2C4)=C1N1CCC(CO)CC1 LVXCVDKHYCXECN-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/16—Halogen atoms or nitro radicals
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/38—Nitrogen atoms
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- 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
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Claims (23)
1. Spoj, naznačen time, da ima sljedeću formulu (I):
[image]
u kojoj:
R1 je vodik;
R2 je adamantan, nesupstituiran ili supstituiran s hidroksi ili halogenom;
R3 je skupina: trifluorometil, pirazol, triazol, piperidin, pirolidin, hidroksimetil-piperidin, benzilpiperazin, hidroksipirolidin, tert-butil-pirolidin, hidroksietil-piperazin, hidroksipiperidin ili tiomorfolin;
R4 je ciklopropil, tert-butil, -C(CH3)2CH2OH, metil, -CF3 ili -(CH2)nCF3-skupina, gdje nje 1 ili 2;
R5 je vodik ili C1-C7-alkil, nesupstituiran ili supstituiran s halogenom;
i njegove farmaceutski podnošljive soli.
2. Spoj prema zahtjevu 1, naznačen time, da
R2 je nesupstituirani adamantan; i
R3 je skupina: trifluorometil, pirazol, triazol, piperidin, pirolidin, hidroksimetil-piperidin, benzilpiperazin, hidroksipirolidin, tert-butil-pirolidin, hidroksietil-piperazin, hidroksipiperidin ili tiomorfolin.
3. Spoj prema zahtjevu 1, naznačen time, da
R2 je adamantan supstituiran s hidroksi ili halogenom; i
R3 je skupina: trifluorometil, pirazol, triazol, piperidin, pirolidin, hidroksimetil-piperidin, benzilpiperazin, hidroksipirolidin, tert-butil-pirolidin, hidroksietil-piperazin, hidroksipiperidin ili tiomorfolin.
4. Spoj prema bilo kojem od zahtjeva 1 i 2, naznačen time, da
R2 je nesupstituirani adamantan; i
R4 je ciklopropil, tert-butil, -C(ΟΗ3)2CΗ2OΗ, metil, -CF3 ili -(CH2)nCF3-skupina, gdje n je 1 ili 2.
5. Spoj prema bilo kojem od zahtjeva 1 i 3, naznačen time, da
R2 je adamantan supstituiran s hidroksi ili halogenom; i
R4 je ciklopropil, tert-butil, -C(CH3)2CH2OH, metil, -CF3 ili -(CH2)nCF3-skupina,
gdje n je 1 ili 2.
6. Spoj prema bilo kojem od zahtjeva 1, 3 i 5, naznačen time, da R2 je trans--hidroksi-adamantan.
7. Spoj prema bilo kojem od zahtjeva 1 do 6, naznačen time, da R3 je trifluorometil-skupina.
8. Spoj prema bilo kojem od zahtjeva 1 do 6, naznačen time, da R3 je skupina: pirazol, triazol, piperidin, pirolidin, hidroksimetil-piperidin, benzilpiperazin, hidroksipirolidin, tert-butil-pirolidin, hidroksietil-piperazin, hidroksipiperidin ili tiomorfolin-skupina.
9. Spoj prema bilo kojem od zahtjeva 1 do 8, naznačen time, da R5 je trifluorometil-skupina.
10. Spoj prema bilo kojem od zahtjeva 1 do 9, naznačen time, da je odabran od sljedećih:
2'-metil-2'H-[1,3']bipirazolil-4'-karboksilna kiselina-adamantan-2-ilamid;
metil-5-trifluorometil-1H-pirazol-4-karboksilna kiselina-adamantan-2-ilamid;
tert-butil-5-trifluorometil-1H-pirazol-4-karboksilna kiselina- adamantan-2-ilamid;
trans-1-tert-butil-5-trifluorometil-1H-pirazol-4-karboksilna kiselina-amid;
cis-1-tert-butil-5-trifluorometil-1H-pirazol-4-karboksilna kiselina-amid;
trans-2'-metil-2'H-[1,3']bipirazolil-4'-karboksilna kiselina-(5-hidroksi-adamantan-2-il)-amid;
ciklopropil-5-trifluorometil-1H-pirazol-4-karboksilna kiselina- adamantan-2-ilamid;
ciklopropil-5-trifluorometil-1H-pirazol-4-karboksilna kiselina-(5-hidroksi-adamantan-2-il)-amid;
metil-5-[1,2,4]triazol-1-il-1H-pirazol-4-karboksilna kiselina-adamantan-2-il amid;
metil-5-pirolidin-1-il-1H-pirazol-4-karboksilna kiselina-adamantan-2-ilamid;
5-(3-hidroksi-pirolidin-1-il)-1-metil-1H-pirazol-4-karboksilna kiselina-adamantan-2-ilamid;
5-(4-hidroksi-piperidin-1-il)-1-metil-1H-pirazol-4-karboksilna kiselina-adamantan-2-ilamid;
metil-5-piperidin-1-il-1H-pirazol-4-karboksilna kiselina-adamantan-2-ilamid;
5-(4-hidroksimetil-piperidin-1-il)-1-metil-1H-pirazol-4-karboksilna kiselina-adamantan-2-ilamid;
5-(4-benzil-piperazin-1-il)-1-metil-1H-pirazol-4-karboksilna kiselina-adamantan-2-ilamid;
5-(R)-3-hidroksi-pirolidin-1-il)-1-metil-1H-pirazol-4-karboksilna kiselina-adamantan-2-ilamid;
tert-butil-5-pirolidin-1-il-1H-pirazol-4-karboksilna kiselina-adamantan-2-ilamid;
5-(4-(2-hidroksi-etil)-piperazin-1-il]-1-metil-1H-pirazol-4-karboksilna kiselina-adamantanilamid;
2'-tert-butil-2'H-[1,3']bipirazolil-4'-karboksilna kiselina-adamantan-2-ilamid;
trans-2'-tert-butil-2'H-[1,3']bipirazolil-4'-karboksilna kiselina-(5-hidroksi-adamantan-2-il )-amid;
tert-butil-5-(3-hidroksi-pirolidin-1-il)-1H-pirazol-4-karboksilna kiselina-adamantan-2-ilamid;
tert-butil-5-(4-hidroksi-piperidin-1-il)-1H-pirazol-4-karboksilna kiselina-adamantan-2-ilamid;
metil-5-tiomorfolin-4-il-1H-pirazol-4-karboksilna kiselina-adamantan-2-ilamid;
tert-butil-5-piperidin-1-il-1H-pirazol-4-karboksilna kiselina-adamantan-2-ilamid;
trans-1-tert-butil-5-trifluorometil-1H-pirazol-4-karboksilna kiselina-(5-fluoro-adamantan-2-il)-amid;
trans-1-ciklopropil-5-trifluorometil-1H-pirazol-4-karboksilna kiselina-(5-hidroksi-adamantan-2-il)-amid;
trans-2'-ciklopropil-2'H-[1,3']bipirazolil-4'-karboksilna kiselina-(5-hidroksi-adamantan-2-il)-amid;
trans-1-(2-hidroksi-1,1-dimetil-etil)-5-trifluorometil-1H-pirazol-4-karboksilna kiselina-(5-hidroksi-adamantan-2-il)-amid;
trans-2'-tert-butil-4-metil-2'H-[1,3']bipirazolil-4'-karboksilna kiselina-(5-hidroksi-adamantan-2-il)-amid; i
trans-2'-tert-butil-4-kloro-2'H-[1,3']bipirazolil-4'-karboksilna kiselina-(5-hidroksi-adamantan-2-il)-amid;
11. Spoj prema bilo kojem od zahtjeva 1 do 10, naznačen time, da je odabran od sljedećih:
trans-2'-tert-butil-2'H-[1,3']bipirazolil-4'-karboksilna kiselina-(5-hidroksi-adamantan-2-il)-amid;
2'-metil-2'H-[1,3']bipirazolil-4'-karboksilna kiselina-adamantan-2-ilamid;
1-metil-5-trifluorometil-1H-pirazol-4-karboksilna kiselina-adamantan-2-ilamid;
trans-1-tert-butil-5-trifluorometil-1H-pirazol-4-karboksilna kiselina-(5-hidroksi-adamantan-2-il)-amid;
cis-1-tert-butil-5-trifluorometil-1H-pirazol-4-karboksilna kiselina-(5-hidroksi-adamantan-2-il)-amid;
trans-2'-metil-2'H-[1,3']bipirazolil-4'-karboksilna kiselina-(5-hidroksi-adamantan-2-il)-amid;
1-ciklopropil-5-trifluorometil-1H-pirazol-4-karboksilna kiselina-(5-hidroksi-adamantan-2-il)-amid; i
2'-tert-butil-2'H-[1,3']bipirazolil-4'-karboksilna kiselina-adamantan-2-ilamid.
12. Spoj prema bilo kojem od zahtjeva 1 do 11, naznačen time, da je navedeni spoj odabran iz skupine koju čine:
trans-1-ciklopropil-5-trifluorometil-1H-pirazol-4-karboksilna kiselina-(5-hidroksi-adamantan-2- il)-amid;
trans-2'-ciklopropil-2'H-[1,3']bipirazolil-4'-karboksilna kiselina-(5-hidroksi-adamantan-2-il)-amid;
trans-1-(2-hidroksi-1,1-dimetil-etil)-5-trifluorometil-1H-pirazol-4-karboksilna kiselina-(5-hidroksi- adamantan-2-il)-amid;
trans-2'-tert-butil-4-metil-2'H-[1,3']bipirazolil-4'-karboksilna kiselina-(5-hidroksi-adamantan-2-il)-amid; i
trans-2'-tert-butil-4-kloro-2'H-[1,3']bipirazolil-4'-karboksilna kiselina-(5-hidroksi-adamantan-2-il)-amid.
13. Spoj prema bilo kojem od zahtjeva 1 do 12, naznačen time, da ga sačinjava trans-2'-tert-butil-2'H-[1,3]bipirazolil-4'-karboksilna kiselina-(5-hidroksi-adamantan-2-il)-amid.
14. Farmaceutski sastav, naznačen time, da obuhvaća terapeutski učinkovitu količinu spoja prema bilo kojem od zahtjeva 1 do 13, ili njegove farmaceutski podnošljive soli, i farmaceutski podnošljive nosače.
15. Farmaceutski sastav prema zahtjevu 14, naznačen time, da navedeni spoj je trans-2'-tert-butil-2'H-[1,3']bipirazolil-4,-karboksilna kiselina-(5-hidroksi-adamantan-2-il)-amid.
16. Spojevi prema bilo kojem od zahtjeva 1 do 13, naznačeni time, da se upotrebljavaju kao terapeutski djelotvorna tvar.
17. Spoj za uporabu prema zahtjevu 16, naznačen time, da navedeni spoj je trans-2'-tert-butil-2'H-[1,3']bipirazolil-4'-karboksilna kiselina-(5-hidroksi-adamantan-2-il)-amid.
18. Spojevi prema bilo kojem od zahtjeva 1 do 13, naznačeni time, da se upotrebljavaju za liječenje dijabetesa, pretilosti ili metaboličkog sindroma.
19. Spoj za uporabu prema zahtjevu 18, naznačen time, da navedeni spoj je trans-2'-tert-butil-2'H-[1,3']bipirazolil-4,-karboksilna kiselina-(5-hidroksi-adamantan-2-il)-amid.
20. Spojevi prema bilo kojem od zahtjeva 1 do 13, naznačeni time, da se upotrebljavaju u proizvodnji lijekova za liječenje metaboličkog poremećaja.
21. Spoj za uporabu prema zahtjevu 20, naznačen time, da navedeni spoj je trans-2'-tert-butil-2'H-[1,3']bipirazolil-4-karboksilna kiselina-(5-hidroksi-adamantan-2-i])-amid.
22. Uporaba spoja prema bilo kojem od zahtjeva 1 do 13, naznačena time, da je za proizvodnju lijekova za liječenje dijabetesa, pretilosti i metaboličkog sindroma.
23. Uporaba prema zahtjevu 22, naznačena time, da je za proizvodnju lijekova za liječenje dijabetesa, pretilosti i metaboličkog sindroma, pri čemu taj spoj je trans-2'-tert-butil-2'H-[1,3']bipirazolil-4'-karboksilna kiselina-(5-hidroksi-adamantan-2-il)-amid.
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| US78483106P | 2006-03-22 | 2006-03-22 | |
| US87527406P | 2006-12-15 | 2006-12-15 | |
| PCT/EP2007/052269 WO2007107470A2 (en) | 2006-03-22 | 2007-03-12 | Pyrazoles as 11-beta-hsd-1 |
| EP07726783.9A EP1999114B1 (en) | 2006-03-22 | 2007-03-12 | Pyrazoles as 11-beta-hsd-1 |
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| HRP20151078TT HRP20151078T1 (hr) | 2006-03-22 | 2015-10-12 | Pirazoli kao 11-beta-hsd-1 |
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| US (1) | US7728029B2 (hr) |
| EP (2) | EP1999114B1 (hr) |
| JP (1) | JP5031817B2 (hr) |
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- 2007-03-12 PL PL07726783T patent/PL1999114T3/pl unknown
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- 2007-03-12 MX MX2008012017A patent/MX2008012017A/es active IP Right Grant
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- 2007-03-12 AU AU2007228887A patent/AU2007228887B2/en not_active Ceased
- 2007-03-12 ES ES07726783.9T patent/ES2548002T3/es active Active
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