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NZ745185B2 - 3-((hetero-)aryl)-8-amino-2-oxo-1,3-diaza-spiro-[4.5]-decane derivatives - Google Patents
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NZ745185B2 - 3-((hetero-)aryl)-8-amino-2-oxo-1,3-diaza-spiro-[4.5]-decane derivatives - Google Patents

3-((hetero-)aryl)-8-amino-2-oxo-1,3-diaza-spiro-[4.5]-decane derivatives Download PDF

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NZ745185B2
NZ745185B2 NZ745185A NZ74518517A NZ745185B2 NZ 745185 B2 NZ745185 B2 NZ 745185B2 NZ 745185 A NZ745185 A NZ 745185A NZ 74518517 A NZ74518517 A NZ 74518517A NZ 745185 B2 NZ745185 B2 NZ 745185B2
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unsubstituted
polysubstituted
mono
unsaturated
saturated
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NZ745185A
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NZ745185A (en
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Ruth Jostock
Achim Kless
Thomas Koch
Rene Michael Koenigs
Ingo Konetzki
Sven Kuhnert
Klaus Linz
Paul Ratcliffe
Wolfgang Schroder
Anita Wegert
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Grünenthal GmbH
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Priority to NZ784118A priority Critical patent/NZ784118B2/en
Priority claimed from PCT/EP2017/025005 external-priority patent/WO2017121647A1/en
Publication of NZ745185A publication Critical patent/NZ745185A/en
Publication of NZ745185B2 publication Critical patent/NZ745185B2/en

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    • 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
    • A61K31/4164—1,3-Diazoles
    • A61K31/4166—1,3-Diazoles having oxo groups directly attached to the heterocyclic ring, e.g. phenytoin
    • A—HUMAN NECESSITIES
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    • 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
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    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • 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
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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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    • C07D417/04—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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    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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    • C07D487/04—Ortho-condensed systems

Abstract

The invention relates to 3-((hetero-)aryl)-8-amino-2-oxo-1,3-diaza-spiro-[4.5]-decane derivatives of formula (I), their preparation and their use in medicine, particularly in the treatment of pain.

Claims (20)

WE CLAIM:
1. A compound according to general formula (I) 13 16 14 15 wherein R and R independently of one another mean -C -C -alkyl, linear or branched, saturated or unsaturated, unsubstituted or substituted with one, two, three or four substituents independently of one another selected from the group consisting of -F, -Cl, -Br, -I, -OH, -OCH , -CN and -CO CH ; 3 2 3 a 3membered cycloalkyl moiety, saturated or unsaturated, unsubstituted or substituted with one, two, three or four substituents independently of one another selected from the group consisting of -F, -Cl, -Br, -I, -OH, -OCH , -CN and -CO CH ; wherein 3 2 3 said 3membered cycloalkyl moiety is optionally connected through -C -C -alkylene- , linear or branched, saturated or unsaturated, unsubstituted; or a 3membered heterocycloalkyl moiety, saturated or unsaturated, unsubstituted or substituted with one, two, three or four substituents independently of one another selected from the group consisting of -F, -Cl, -Br, -I, -OH, -OCH , -CN and -CO CH ; wherein 3 2 3 said 3membered heterocycloalkyl moiety is optionally connected through -C -C - alkylene-, linear or branched, saturated or unsaturated, unsubstituted; R and R together with the nitrogen atom to which they are attached form a ring and mean -(CH ) -; -(CH ) -O-(CH ) -; or -(CH ) -NR -(CH ) -, wherein R means -H or 2 3-6 2 2 2 2 2 2 2 2 -C -C -alkyl, linear or branched, saturated or unsaturated, unsubstituted or substituted with one, two, three or four substituents independently of one another selected from the group consisting of -F, -Cl, -Br and -I; R means -C -C -alkyl, linear or branched, saturated or unsaturated, unsubstituted, mono- or polysubstituted; a 3membered cycloalkyl moiety, saturated or unsaturated, unsubstituted, mono- or polysubstituted; wherein said 3membered cycloalkyl moiety is optionally connected through -C -C -alkylene-, linear or branched, saturated or unsaturated, unsubstituted, mono- or polysubstituted; a 3membered heterocycloalkyl moiety, saturated or unsaturated, unsubstituted, mono- or polysubstituted; wherein said 3membered heterocycloalkyl moiety is optionally connected through -C -C -alkylene-, linear or branched, saturated or unsaturated, unsubstituted, mono- or polysubstituted; a 6membered aryl moiety, unsubstituted, mono- or polysubstituted; wherein said 6- 14-membered aryl moiety is optionally connected through -C -C -alkylene-, linear or branched, saturated or unsaturated, unsubstituted, mono- or polysubstituted; or a 5membered heteroaryl moiety, unsubstituted, mono- or polysubstituted; wherein said 5membered heteroaryl moiety is optionally connected through -C -C -alkylene- , linear or branched, saturated or unsaturated, unsubstituted, mono- or polysubstituted; R means -C -C -alkyl, linear or branched, saturated or unsaturated, unsubstituted, mono- or polysubstituted; wherein said -C -C -alkyl is optionally connected through -C(=O)-, - C(=O)O-, or -S(=O) -; a 3membered cycloalkyl moiety, saturated or unsaturated, unsubstituted, mono- or polysubstituted; wherein said 3membered cycloalkyl moiety is optionally connected through -C -C -alkylene-, linear or branched, saturated or unsaturated, unsubstituted, mono- or polysubstituted; or wherein said 3membered cycloalkyl moiety is optionally connected through -C(=O)-, -C(=O)O-, -C(=O)O-CH -, or -S(=O) -; a 3membered heterocycloalkyl moiety, saturated or unsaturated, unsubstituted, mono- or polysubstituted; wherein said 3membered heterocycloalkyl moiety is optionally connected through -C -C -alkylene-, linear or branched, saturated or unsaturated, unsubstituted, mono- or polysubstituted; or wherein said 3membered heterocycloalkyl moiety is optionally connected through -C(=O)-, -C(=O)O-, -C(=O)O- CH -, or -S(=O) -; a 6membered aryl moiety, unsubstituted, mono- or polysubstituted; wherein said 6- 14-membered aryl moiety is optionally connected through -C -C -alkylene-, linear or branched, saturated or unsaturated, unsubstituted, mono- or polysubstituted; or wherein said 6membered aryl moiety is optionally connected through -C(=O)-, -C(=O)O-, - C(=O)O-CH -, or -S(=O) -; or a 5membered heteroaryl moiety, unsubstituted, mono- or polysubstituted; wherein said 5membered heteroaryl moiety is optionally connected through -C -C -alkylene- , linear or branched, saturated or unsaturated, unsubstituted, mono- or polysubstituted; or wherein said 5membered heteroaryl moiety is optionally connected through -C(=O)- , -C(=O)O-, -C(=O)O-CH -, or -S(=O) -; R means a 6membered aryl moiety, unsubstituted, mono- or polysubstituted; or a 5membered heteroaryl moiety, unsubstituted, mono- or polysubstituted; 11 12 13 14 15 16 17 18 19 20 R , R , R , R , R , R , R , R , R , and R independently of one another mean - H, -F, -Cl, -Br, -I, -OH, or -C -C -alkyl, linear or branched, saturated or unsaturated, unsubstituted, mono- or polysubstituted; wherein "mono- or polysubstituted" means that one or more hydrogen atoms are replaced by a substituent independently of one another selected from the group consisting of -F, - 21 21 21 21 22 Cl, -Br, -I, -CN, -R , -C(=O)R , -C(=O)OR , -C(=O)NR R , -C(=O)NH-(CH CH - 21 21 O) -CH , -O-(CH CH -O) -H, -O-(CH CH -O) -CH , =O, -OR , -OC(=O)R , - 1-30 3 2 2 1-30 2 2 1-30 3 21 21 22 21 22 21 22 21 OC(=O)OR , -OC(=O)NR R , -NO , -NR R , -NR -(CH ) -C(=O)R , -NR - 2 2 1-6 22 23 21 22 21 22 21 (CH ) -C(=O)OR , -NR -(CH ) -C(=O)NR R , -NR C(=O)R , -NR C(=O)- 2 1-6 2 1-6 22 23 21 22 21 22 21 21 21 OR , -NR C(=O)NR R , -NR S(=O) R , -SR , -S(=O)R , -S(=O) R , - 21 21 22 S(=O) OR , and -S(=O) NR R ; wherein 21 22 23 R , R and R independently of one another mean -C -C -alkyl, linear or branched, saturated or unsaturated, unsubstituted or substituted with one, two, three or four substituents independently of one another selected from the group consisting of -F, -Cl, -Br, -I, -CN, -OH, -NH , -CO H, -C(=O)O-C -C -alkyl, - 2 2 1 6 C(=O)NH , -C(=O)NHC -C -alkyl, -C(=O)N(C -C -alkyl) , -O-C -C -alkyl and - 2 1 6 1 6 2 1 6 S(=O) -C -C -alkyl; 2 1 6 a 3membered cycloalkyl moiety, saturated or unsaturated, unsubstituted, mono- or polysubstituted; wherein said 3membered cycloalkyl moiety is optionally connected through -C -C -alkylene-, linear or branched, saturated or unsaturated, unsubstituted or substituted with one, two, three or four substituents independently of one another selected from the group consisting of -F, -Cl, -Br, -I, -CN, -OH, -NH , -C -C -alkyl and -O-C - 2 1 6 1 C -alkyl; a 3membered heterocycloalkyl moiety, saturated or unsaturated, unsubstituted, mono- or polysubstituted; wherein said 3membered heterocycloalkyl moiety is optionally connected through -C -C -alkylene-, linear or branched, saturated or unsaturated, unsubstituted or substituted with one, two, three or four substituents independently of one another selected from the group consisting of -F, -Cl, -Br, -I, -CN, -OH, -NH , -C -C -alkyl and -O-C -C -alkyl; 2 1 6 1 6 a 6membered aryl moiety, unsubstituted, mono- or polysubstituted; wherein said 6- 14-membered aryl moiety is optionally connected through -C -C -alkylene-, linear or branched, saturated or unsaturated, unsubstituted or substituted with one, two, three or four substituents independently of one another selected from the group consisting of -F, -Cl, -Br, -I, -CN, -OH, -NH , -C -C -alkyl and -O-C -C -alkyl; 2 1 6 1 6 a 5membered heteroaryl moiety, unsubstituted, mono- or polysubstituted; wherein said 5membered heteroaryl moiety is optionally connected through -C -C -alkylene- , linear or branched, saturated or unsaturated, unsubstituted or substituted with one, two, three or four substituents independently of one another selected from the group consisting of -F, -Cl, -Br, -I, -CN, -OH, -NH , -C -C -alkyl and -O-C -C -alkyl; 2 1 6 1 6 21 22 21 22 21 22 21 22 23 or R and R within -C(=O)NR R , -OC(=O)NR R , -NR R , -NR -(CH ) - 2 1-6 21 22 23 21 22 21 22 C(=O)NR R , -NR C(=O)NR R , or -S(=O) NR R together with the nitrogen atom to which they are attached form a ring and mean -(CH ) -; -(CH ) -O-(CH ) -; - 2 3-6 2 2 2 2 (CH ) -S(=O) -(CH ) - or -(CH ) -NR -(CH ) -, wherein R means -H, -C -C -alkyl, - 2 2 2 2 2 2 2 2 2 1 6 C(=O)-C -C -alkyl, or -S(=O) -C -C -alkyl, wherein said C -C -alkyl is linear or 1 6 2 1 6 1 6 branched, saturated or unsaturated, unsubstituted or substituted with one, two, three or four substituents independently of one another selected from the group consisting of -F, -Cl, -Br, -I, -OH, -CO H, -C(=O)O-C -C -alkyl and -C(=O)NH ; and wherein said ring 2 1 6 2 is unsubstituted or substituted with one, two, three or four substituents independently of one another selected from the group consisting of -F, -Cl, -Br, -I, -CN, =O, -OH, -NH , - C -C -alkyl and -O-C -C -alkyl; 1 6 1 6 or a physiologically acceptable salt thereof. 11 12 13 14 15 16 17 18 19
2. The compound according to claim 1, wherein R , R , R , R , R , R , R , R , R , and R independently of one another mean -H, -F, -OH, or -C -C -alkyl.
3. The compound according to claim 1 or 2, wherein R means -H; and R means -C1-C6- alkyl, linear or branched, saturated or unsaturated, unsubstituted, mono- or polysubstituted.
4. The compound according to claim 1 or 2, wherein R means -CH ; and R means -C - C -alkyl, linear or branched, saturated or unsaturated, unsubstituted, mono- or polysubstituted.
5. The compound according to claim 1 or 2, wherein R means -H or -CH ; and wherein R means -CH -cycloalkyl, -CH -cyclobutyl, -CH -cyclopentyl, -CH -oxetanyl or -CH - 2 2 2 2 2 tetrahydrofuranyl.
6. The compound according to claim 1 or 2, wherein R and R together with the nitrogen atom to which they are attached form a ring and mean -(CH2)3.
7. The compound according to any one of the preceding claims, wherein R means -C -C - alkyl, linear or branched, saturated or unsaturated, unsubstituted, mono- or polysubstituted.
8. The compound according to any one of claims 1 to 6, wherein R means a 6 membered aryl moiety, unsubstituted, mono- or polysubstituted.
9. The compound according to any one of claims 1 to 6, wherein R means a 5 membered heteroaryl moiety, unsubstituted, mono- or polysubstituted.
10. The compound according to any one of the preceding claims, wherein R means -H.
11. The compound according to any one of claims 1 to 9, wherein R means -C -C -alkyl, linear or branched, saturated or unsaturated, unsubstituted, mono- or polysubstituted.
12. The compound according to any one of claims 1 to 9, wherein R means a 3 membered cycloalkyl moiety, saturated or unsaturated, unsubstituted, mono- or polysubstituted; wherein the 3membered cycloalkyl moiety is connected through - C -C -alkylene-, linear or branched, saturated or unsaturated, unsubstituted, mono- or polysubstituted.
13. The compound according to any one of claims 1 to 9, wherein R means a 3 membered heterocycloalkyl moiety, saturated or unsaturated, unsubstituted, mono- or polysubstituted; wherein said 3membered heterocycloalkyl moiety is connected through -C -C -alkylene-, linear or branched, saturated or unsaturated, unsubstituted, mono- or polysubstituted.
14. The compound according to any one of claims 1 to 9, wherein R means a 6 membered aryl moiety, unsubstituted, mono- or polysubstituted; wherein said 6 membered aryl moiety is connected through -C -C -alkylene-, linear or branched, saturated or unsaturated, unsubstituted, mono- or polysubstituted.
15. The compound according to any one of claims 1 to 9, wherein R means a 5 membered heteroaryl moiety, unsubstituted, mono- or polysubstituted; wherein said 5- 14-membered heteroaryl moiety is connected through -C -C -alkylene-, linear or branched, saturated or unsaturated, unsubstituted, mono- or polysubstituted.
16. The compound according to any one of the preceding claims, wherein R means -phenyl, unsubstituted, mono- or polysubstituted.
17. The compound according to any one of claims 1 to 15, wherein R means a monocyclic 5membered heteroaryl moiety, unsubstituted, mono- or polysubstituted.
18. The compound according to any one of claims 1 to 15, wherein R means a bicyclic 9- 10-membered heteroaryl moiety, unsubstituted, mono- or polysubstituted.
19. The compound according to claim 17 or 18, wherein R means -1,2-benzodioxole, - pyrazinyl, -pyridazinyl, -pyridinyl, -pyrimidinyl, -thienyl, -imidazolyl, -benzimidazolyl, -thiazolyl, -1,3,4-thiadiazolyl, -benzothiazolyl, -oxazolyl, -benzoxazolyl, -pyrazolyl, - quinolinyl, -isoquinolinyl, -quinazolinyl, -indolyl, -indolinyl, - benzo[c][1,2,5]oxadiazolyl, -imidazo[1,2-a]pyrazinyl, or -1H-pyrrolo[2,3-b]pyridinyl, in each case unsubstituted, mono- or polysubstituted.
20. The compound according to any one of the preceding claims, which has a structure according to any one of general formulas (II-A) to (VIII-C): (II-A) (II-B) (II-C) (III-A) (III-C) (III-B) (CH ) (CH ) 2 2-3 2 2-3 H CO H CO (IV-A) (IV-B) (CH ) 2 2-3 (IV-C) (V-A) (V-C) (V-B) (CH ) (CH ) 2 2-3 2 2-3 H CO 3 (VI-B) (VI-A) (CH ) 2 2-3 (VII-A) D (VI-C)
NZ745185A 2017-01-13 3-((hetero-)aryl)-8-amino-2-oxo-1,3-diaza-spiro-[4.5]-decane derivatives NZ745185B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
NZ784118A NZ784118B2 (en) 2017-01-13 3-((hetero-)aryl)-8-amino-2-oxo-1,3-diaza-spiro-[4.5]-decane derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP16151012 2016-01-13
PCT/EP2017/025005 WO2017121647A1 (en) 2016-01-13 2017-01-13 3-((hetero-)aryl)-8-amino-2-oxo-1,3-diaza-spiro-[4.5]-decane derivatives

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NZ745185A NZ745185A (en) 2024-03-22
NZ745185B2 true NZ745185B2 (en) 2024-06-25

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