Back to results
US 2007/0185079 A1Published application
Therapeutic agents I
AssigneeAstraZeneca AB
InventorsEmma Evertsson, Tord Inghardt, Jan Lindberg, Anna Linusson, Fabrizio Giordanetto
Life of this patent
Estimating the term…
Abstract
Compounds of formula(I), processes for preparing such compounds, their use in the treatment of obesity, psychiatric disorders, cognitive disorders, memory disorders, schizophrenia, epilepsy, and related conditions, and neurological disorders such as dementia, multiple sclerosis, Parkinson's disease, Huntington's chorea and Alzheimer's disease and pain related disorders, and pharmaceutical compositions containing them.
Claims21
A compound of formula I
- wherein
- R1 represents a C1-4 alkoxy group optionally substituted by one or more fluoro, a C1-4 alkyl group optionally substituted by one or more fluoro, halo, cyano, a group OSO2C1-4alkyl wherein the alkyl group is optionally substituted with one or more fluorine atoms, a group NRaRb in which Ra and Rb independently represent H or a C1-4alkyl group or Ra and Rb together with the nitrogen atom to which they are attached represent a saturated 3 to 7 membered heterocyclic ring optionally including an O, a group CONRcRd in which Rc and Rd independently represent H or a C1-4alkyl group or Rc and Rd together with the nitrogen atom to which they are attached represent a saturated 3 to 7 membered heterocyclic ring;
- n represents 0, 1, 2 or 3;
- R2 represents a C1-4alkyl group optionally substituted by one or more fluoro or a C1-4alkoxy group optionally substituted by one or more fluoro, a group NRaRb in which Ra and Rb independently represent H or a C1-4 alkyl group or Ra and Rb together with the nitrogen atom to which they are attached represent a saturated 3 to 7 membered heterocyclic ring optionally including an O, a group CONRcRd in which Rc and Rd independently represent H or a C1-4alkyl group or Rc and Rd together with the nitrogen atom to which they are attached represent a saturated 3 to 7 membered heterocyclic ring;
- m represents 0 or 1;
- R3 represents H or a C1-4 alkyl group;
- L1 represents a (CH2)pC3-10 cycloalkyl(CH2)q group in which p and q are independently selected from 0 and 1 and in which the cycloalkyl group may be monocyclic or bicyclic and optionally may be bridged provided that the two nitrogens bearing R3 and R4, respectively, are not linked to the same carbon atom, and wherein one of the carbons may be replaced by O or, alternatively, the group —N(R3)-L1- or the group L1-N(R4) together represent a saturated bicyclic heterocyclic ring containing from 2 to 9 carbon atoms and the nitrogen bearing R3 or R4 respectively;
- R4 represents H or a C1-4 alkyl group optionally substituted by one or more of the following:
- fluoro or C1-4 alkoxy optionally substituted by one or more fluoro;
- L2 represents an alkylene chain (CH2)s, in which s represents 1, 2 or 3 wherein the alkylene chain is optionally substituted by one or more of the following:
- fluoro or C1-4 alkyl;
- or L2 may also represent a 5-6 membered carbocyclic ring fused to R5;
- R5 represents phenyl or naphthyl or a heterocyclic group selected from thienyl, furyl, pyridyl, pyrrolyl, quinolinyl, indolyl, benzofuranyl, benzo[b]thienyl, imidazolyl, benzimidazolyl, thiazolyl, thiadiazolyl, pyrimidinyl, pyrazolyl, oxazolyl, imidazo[1,2-a]pyridinyl, 5H-pyrrolo[2,3-b]pyrazinyl, 1H-pyrrolo[3,2-c]pyridinyl, 1H-pyrrolo[2,3-c]pyridinyl, 1H-pyrrolo[2,3-b]pyridinyl, 1H-indazolyl, 1H-pyrrolo[3,2-h]quinolinyl, 1H-pyrrolo[3,2-b]pyridinyl, 2,1,3-benzothiadiazolyl, 2,1,3-benzoxadiazolyl, quinazolinyl or triazolyl wherein each R5 is optionally substituted by one or more of the following:
- cyano, halo, a C1-4 alkyl group optionally substituted by one or more fluoro, a C1-4 alkoxy group optionally substituted by one or more fluoro, or by a group S(O)aRy in which a is 0, 1 or 2 and Ry is phenyl optionally substituted by cyano, halo, a C1-4alkyl group optionally substituted by one or more fluoro or a C1-4alkoxy group optionally substituted by one or more fluoro, or by a group Oz(CH2)wRz in which z and w independently are 0 or 1 and Rz represents phenyl or a heterocyclic group selected from thienyl, pyridyl, thiazolyl, pyrazolyl, wherein each Rz is optionally substituted by one or more of the following:
- cyano, halo, a C1-4 alkyl group optionally substituted by one or more fluoro, or a C1-4alkoxy group optionally substituted by one or more fluoro;
- as well as optical isomers and racemates thereof as well as pharmaceutically acceptable salts, thereof;
- with the proviso that when
- R1 represents a C1-4alkoxy group optionally substituted by one or more fluoro or a C1-4alkyl group optionally substituted by one or more fluoro;
- and
- n represents 0 or 1;
- and
- R2 represents a C1-4alkyl group optionally substituted by one or more fluoro or a C1-4alkoxy group optionally substituted by one or more fluoro;
- and
- m represents 0 or 1;
- and
- R3 represents H or a C1-4alkyl group;
- and
- L1 represents a cyclohexyl group wherein the two nitrogens bearing R3 and R4, respectively, are linked to the cyclohexyl group either via the 1,3 or the 1,4 positions of the cyclohexyl group or L1 represents a cyclopentyl group wherein the two nitrogens bearing R3 and R4, respectively, are linked to the cyclopentyl group via the 1,3 position of the cyclopentyl group;
- and
- L2 represents an alkylene chain (CH2), in which s represents 1, 2 or 3 wherein the alkylene chain is optionally substituted by one or more of the following:
- a C1-4alkyl group;
- and
- R5 represents aryl wherein aryl means phenyl or naphthyl each of which is optionally substituted by one or more of the following:
- halo, a C1-4alkyl group or phenyl, or
- R5 represents a heterocyclic group wherein the term heterocyclic group means thienyl, furyl, pyridyl, pyrrolyl, quinolinyl, indolyl, benzofuranyl or benzo[b]thienyl each of which is optionally substituted by one or more of the following:
- halo or a C1-4alkyl group;
- or L2 represents a C5-6cycloalkyl group which is fused to an R5 which is phenyl or a heteroaryl group selected from thienyl, furyl or pyrrolyl;
- then R4 does not represent H or a C1-4alkyl group;
- and excluding 1,4-anhydro-2,3,5-trideoxy-3-[[(3,4-dichlorophenyl)methyl]amino]-5-[(4-ethoxy-2-quinolinyl)amino]-D-erythro-pentitol.
36 more elements
A compound of formula IA
- in which
- R1 represents chloro, fluoro, methoxy or a group NRaRb in which Ra and Rb independently represent H or a C1-4alkyl group;
- n represents 0, 1 or 2 and when n=1 the substituent is attached to either position 6 or 7;
- R2 represents a C1-4alkyl group or a C1-4alkoxy group optionally substituted by one or more fluoro, a group NRaRb in which Ra and Rb independently represent H or a C1-4alkyl group or Ra and Rb together with the nitrogen atom to which they are attached represent a saturated 3 to 7 membered heterocyclic ring optionally including an O, a group CONRcRd in which R1 and Rd independently represent H or a C1-4alkyl group or Rc and Rd together with the nitrogen atom to which they are attached represent a saturated 3 to 7 membered heterocyclic ring;
- m represents 0 or 1;
- R3 represents H;
- A represents CH2 and t is 0 or 1;
- R4 represents H;
- L2 represents CH2, C(CH3)2 or CF2;
- and
- R5 represents aryl or a heterocyclic group selected from thienyl, furyl, pyridyl, pyrrolyl, quinolinyl, indolyl, benzofuranyl, benzo[b]thienyl, imidazolyl, benzimidazolyl, thiazolyl, thiadiazolyl, pyrimidinyl, pyrazolyl, oxazolyl, imidazo[1,2-a]pyridine, 5H-pyrrolo[2,3-b]pyrazine, 1H-pyrrolo[3,2-c]pyridine, 1H-pyrrolo[2,3-c]pyridine, 1H-pyrrolo[2,3-b]pyridine, 1H-indazole each of which is optionally substituted by one or more of the following:
- cyano, halo, a C1-4 alkyl group optionally substituted by one or more fluoro, a C1-4 alkoxy group optionally substituted by one or more fluoro, or by a group S(O)aRy in which a is 0, 1 or 2 and Ry is phenyl optionally substituted by cyano, halo, a C1-4alkyl group optionally substituted by one or more fluoro or a C1-4alkoxy group optionally substituted by one or more fluoro, or by a group Oz(CH2)wRz in which z and w independently are 0 or 1 and Rz represents phenyl or a heterocyclic group selected from thienyl, pyridyl, thiazolyl, pyrazolyl, wherein each Rz is optionally substituted by one or more cyano, halo, a C1-4 alkyl group optionally substituted by one or more fluoro, a C1-4alkoxy group optionally substituted by one or more fluoro;
- as well as optical isomers and racemates thereof as well as pharmaceutically acceptable salts thereof.
10 more elements
A compound of formula IB
- in which
- R1 represents H, methoxy, dimethylamino, chloro or fluoro;
- R2 represents H, a C1-4alkyl group or a C1-4 alkoxy group optionally substituted by one or more fluoro, a group NRaRb in which Ra and Rb independently represent H or a C1-4alkyl group or Ra and Rb together with the nitrogen atom to which they are attached represent a saturated 3 to 7 membered heterocyclic ring optionally including an O, a group CONRcRd in which Rc and Rd independently represent H or a C1-4alkyl group or Rc and Rd together with the nitrogen atom to which they are attached represent a saturated 3 to 7 membered heterocyclic ring;
- R3 represents H;
- A represents CH2 and t is 0 or 1;
- R4 represents H;
- L2 represents CH2, C(CH3)2 or CF2;
- and
- R5 represents 2-thienyl, 3-thienyl, indol-3-yl, 2-pyrrolyl, 5-pyrimidinyl, 4-thiadiazolyl, pyrazolyl, or quinolin-2-yl each of which is optionally substituted by one or more of the following:
- cyano, halo, a C1-4 alkyl group optionally substituted by one or more fluoro, a C1-4 alkoxy group optionally substituted by one or more fluoro and in addition when R5 is 2-thienyl it is optionally additionally substituted by pyridyl, 2-thienyl or 3-pyrazolyl each of which is optionally substituted by halo or a C1-4 alkyl group optionally substituted by one or more fluoro and when R5 is indol-3-yl it is optionally additionally substituted by 1-(thiazol-5-yl)methyl which is optionally substituted by halo.
7 more elements
A compound of formula IC
- in which xR1 represents H, methoxy, dimethylamino, chloro or fluoro;
- R2 represents H, a C1-4alkyl group or a C1-4 alkoxy group optionally substituted by one or more fluoro, a group NRaRb in which Ra and Rb independently represent H or a C1-4alkyl group or Ra and Rb together with the nitrogen atom to which they are attached represent a saturated 3 to 7 membered heterocyclic ring optionally including an O, a group CONRcRd in which Rc and Rd independently represent H or a C1-4alkyl group or Rc and Rd together with the nitrogen atom to which they are attached represent a saturated 3 to 7 membered heterocyclic ring;
- R3 represents H;
- A represents CH2 and t is 0 or 1;
- R4 represents H;
- L2 represents CH2, C(CH3)2 or CF2;
- and
- R5 represents 2-thienyl, 3-thienyl, indol-3-yl, 2-pyrrolyl, 5-pyrimidinyl, 4-thiadiazolyl, pyrazolyl, 1H-pyrrolo[3,2-b]pyridinyl or quinolin-2-yl each of which is optionally substituted by one or more of the following:
- cyano, halo, a C1-4 alkyl group optionally substituted by one or more fluoro, a C1-4 alkoxy group optionally substituted by one or more fluoro and in addition when R5 is 2-thienyl it is optionally additionally substituted by pyridyl, 2-thienyl or 3-pyrazolyl each of which is optionally substituted by halo or a C1-4 alkyl group optionally substituted by one or more fluoro and when R5 is indol-3-yl it is optionally additionally substituted by 1-(thiazol-5-yl)methyl which is optionally substituted by halo.
6 more elements
One or more of the following compounds:
- N,N-dimethyl-2-[(3-{[(5-pyridin-2-yl-2-thienyl)methyl]amino}cyclohexyl)amino]-quinoline-4-carboxamide;
- (1S,3S)-N-(6-chloro-4-methylquinolin-2-yl)-N′-[(1-methyl-1H-indol-3-yl)methyl]cyclohexane-1,3-diamine;
- (1S,3S)-N-(6-fluoro-4-methylquinolin-2-yl)-N′-(3-thienylmethyl)cyclohexane-1,3-diamine;
- (1R,3R)-N-(6-fluoro-4-methylquinolin-2-yl)-N′-(3-thienylmethyl)cyclohexane-1,3-diamine;
- (1S,3S)-N-(6-fluoro-4-methoxyquinolin-2-yl)-N′-(3-thienylmethyl)cyclohexane-1,3-diamine;
- (1S,3S)-N-(6-fluoro-4-methylquinolin-2-yl)-N′-[(1-methyl-1H-indol-3-yl)methyl]cyclopentane-1,3-diamine;
- N-(6-chloroquinolin-2-yl)-N′-(3-thienylmethyl)cyclohexane-1,3-diamine;
- N-(6-chloroquinolin-2-yl)-N′-[(1-methyl-1H-pyrrol-2-yl)methyl]cyclohexane-1,3-diamine;
- N-(6-chloroquinolin-2-yl)-N′-(quinolin-3-ylmethyl)cyclohexane-1,3-diamine;
- N6,N6-dimethyl-N2-{3-[(3-thienylmethyl)amino]cyclohexyl}quinoline-2,6-diamine;
- (1S,3S)-N-[(4-chloro-1-methyl-1H-pyrazol-3-yl)methyl]-N′-(6-methoxy-4-methylquinolin-2-yl) cyclopentane-1,3-diamine;
- (1S,3S)-N-(6-methoxy-4-methylquinolin-2-yl)-N′-(1,2,3-thiadiazol-4-ylmethyl)cyclopentane-1,3-diamine;
- (1S,3S)-N-(6-methoxy-4-methylquinolin-2-yl)-N′-[(5-pyridin-2-yl-2-thienyl)methyl]cyclopentane-1,3-diamine;
- (1S,3S)-N-({1-[(2-chloro-1,3-thiazol-5-yl)methyl]-1H-indol-3-yl}methyl)-N′-(6-methoxy-4-methylquinolin-2-yl)cyclopentane-1,3-diamine;
- (1S,3S)-N-(6-methoxy-4-methylquinolin-2-yl)-N′-({5-[1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-2-thienyl}methyl)cyclopentane-1,3-diamine;
- (1S,3S)-N-(2,2′-bithien-5-ylmethyl)-N′-(6-methoxy-4-methylquinolin-2-yl)cyclopentane-1,3-diamine;
- N4,N4-dimethyl-N2-{3-[(3-thienylmethyl)amino]cyclohexyl}quinoline-2,4-diamine;
- N4,N4-dimethyl-N2-[3-({[2-(phenylsulfonyl)-1,3-thiazol-5-yl]methyl}amino)-cyclohexyl]quinoline-2,4-diamine;
- N2-(3-{[(2,4-dimethoxypyrimidin-5-yl)methyl]amino}cyclohexyl)-N4,N4-dimethylquinoline-2,4-diamine;
- 3-(6-methoxy-4-methylquinolin-2-yl)-N-methyl-N-(3-thienylmethyl)-3-azabicyclo[3.2.1]octan-8-amine;
- 6-methoxy-4-methyl-N-[((1R,2S)-2-{[(1-methyl-1H-indol-3-yl)methyl]amino}cyclopentyl)methyl]quinolin-2-amine;
- (1S,3S)-N-(6-fluoro-4-methylquinolin-2-yl)-N′-[(1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl) methyl]cyclopentane-1,3-diamine;
- (1S,3S)-3-[({3-[(7-methoxy-4-methylquinolin-2-yl)amino]cyclopentyl}amino)methyl]-1-methyl-1H-indole-6-carbonitrile;
- (1S,3S)-N-(6-fluoro-4-methylquinolin-2-yl)-N′-[(1-methyl-1H-indol-2-yl)methyl]cyclopentane-1,3-diamine;
- (1S,3S)-N-(6-fluoro-4-methylquinolin-2-yl)-N′-({1-[3-(trifluoromethyl)pyridin-2-yl]-1H-indol -3-yl}methyl)cyclopentane-1,3-diamine;
- (1S,3S)-N-(6-fluoro-4-methylquinolin-2-yl)-N′-[(1-methyl-1H-indazol-3-yl)methyl]cyclopentane-1,3-diamine;
- (1S,3S)-N-(7-methoxy-4-methylquinolin-2-yl)-N′-({1-[4-(trifluoromethyl)phenyl]-1H-pyrrol-3-yl}methyl) cyclopentane-1,3-diamine;
- 3-[({(1S,3S)-3-[(7-methoxy-4-methylquinolin-2-yl)amino]cyclopentyl}amino)methyl]-1-methyl-1H-indole-5-carbonitrile;
- (1S,3S)-N-{[5-difluormethoxy-1H-indol-3-yl]methyl}-N′-(7-methoxy-4-methylquinolin-2-yl)cyclopentane-1,3-diamine;
- (1S,2S,4R,6S)-N-(6-methoxy-4-methylquinolin-2-yl)-N′-(3-thienylmethyl)bicyclo[2.2.1 ]heptane-2,6-diamine;
- (1R,2S,4S,6S)-N-(6-methoxy-4-methylquinolin-2-yl)-N′-(3-thienylmethyl)bicyclo[2.2.1]heptane-2,6-diamine;
- (1S,2S,4R,6S)-N-(7-methoxy-4-methylquinolin-2-yl)-N′-[(1-methyl-1H-indol-3-yl) methyl]bicyclo[2.2.1]heptane-2,6-diamine;
- 6-methoxy-4-methyl-N-[(1S,2R)-2-({[(1-methyl-1H-indol-3-yl)methyl]amino}methyl)cyclopentyl]quinolin-2-amine;
- (1S,3S)-N-(7-methoxy-4-methylquinolin-2-yl)-N′-[(1-methyl-1H-pyrrolo[3,2-h]quinolin-3-yl)methyl]cyclopentane-1,3-diamine;
- (1S,3S)-N-(6-fluoro-4-methylquinolin-2-yl)-N′-[(1-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl) methyl]cyclopentane-1,3-diamine;
- (1S,3S)-N-(7-methoxy-4-methylquinolin-2-yl)-N′-[(1-methyl-1H-pyrrolo[3,2-b]pyridin-3-yl) methyl]cyclopentane-1,3-diamine;
- (1S,3S)-N-(6-fluoro-4-methylquinolin-2-yl)-N′-(imidazo[1,2-a]pyridin-3-ylmethyl) cyclopentane-1,3-diamine;
- (1S,3S)-N-{[5-(Benzyloxy)-1-methyl-1H-indol-3-yl]methyl}-N′-(7-methoxy-4-methylquinolin-2-yl) cyclopentane-1,3-diamine;
- (1S,3S)-N-(7-Methoxy-4-methylquinolin-2-yl)-N′-[3-(trifluoromethoxy)benzyl]-cyclohexane-1,3-diamine;
- (1S,3S)-N-(2,1,3-Benzothiadiazol-4-ylmethyl)-N′-(7-methoxy-4-methylquinolin-2-yl) cyclohexane-1,3-diamine;
- (1S,3S)-N-[(1,3-Dimethyl-1H-pyrazol-4-yl)methyl]-N′-(7-methoxy-4-methylquinolin-2-yl)cyclohexane-1,3-diamine;
- and
- (1S,3S)-N-(2-Bromo-4-methoxybenzyl)-N′-(7-methoxy-4-methylquinolin-2-yl)cyclohexane-1,3-diamine;
- and pharmaceutically acceptable salts thereof.
41 more elements
(canceled)
(canceled)
(canceled)
A process for the preparation of a compound of formula I
- comprising reacting a compound of formula II
- in which
- R1 represents a C1-4alkoxy group optionally substituted by one or more fluoro, a C1-4 alkyl group optionally substituted by one or more fluoro, halo, cyano, a group OSO2C1-4 alkyl wherein the alkyl group is optionally substituted with one or more fluorine atoms, a group NRaRb in which Ra and Rb independently represent H or a C1-4alkyl group or Ra and Rb together with the nitrogen atom to which they are attached represent a saturated 3 to 7 membered heterocyclic ring optionally including an O, a group CONRcR in which Rc and Rd independently represent H or a C1-4alkyl group or Rc and Rd together with the nitrogen atom to which they are attached represent a saturated 3 to 7 membered heterocyclic ring;
- n represents 0, 1, 2 or 3;
- R2 represents a C1-4alkyl group optionally substituted by one or more fluoro or a C1-4alkoxy group optionally substituted by one or more fluoro, a group NRaRb in which Ra and Rb independently represent H or a C1-4 alkyl group or Ra and Rb together with the nitrogen atom to which they are attached represent a saturated 3 to 7 membered heterocyclic ring optionally including an O, a group CONRcRd in which Rc and Rd independently represent H or a C1-4alkyl group or Rc and Rd together with the nitrogen atom to which they are attached represent a saturated 3 to 7 membered heterocyclic ring;
- m represents 0 or 1;
- R3 represents H or a C1-4 alkyl group;
- L1 represents a (CH2)pC3-10 cycloalkyl(CH2)q group in which p and q are independently selected from 0 and 1 and in which the cycloalkyl group may be monocyclic or bicyclic and optionally may be bridged provided that the two nitrogens bearing R3 and R4, respectively, are not linked to the same carbon atom, and wherein one of the carbons may be replaced by O or, alternatively, the group —N(R3)-L1- or the group L1-N(R4) together represent a saturated bicyclic heterocyclic ring containing from 2 to 9 carbon atoms and the nitrogen bearing R3 or R4 respectively;
- R4 represents H or a C1-4 alkyl group optionally substituted by one or more of the following:
- fluoro or C1-4 alkoxy optionally substituted by one or more fluoro;
- with a compound of formula III
- R5-L2′=O III
- in which R5 is as previously defined and L2′ represents a group which after reaction of compounds II and III gives L2 on reduction, under reductive alkylation conditions.
10 more elements
A compound of formula II
- in which
- R1 represents a C1-4 alkoxy group optionally substituted by one or more fluoro, a C1-4 alkyl group optionally substituted by one or more fluoro, halo, cyano, a group OSO2C1-4alkyl wherein the alkyl group is optionally substituted with one or more fluorine atoms, a group NRaRb in which Ra and Rb independently represent H or a C1-4alkyl group or Ra and Rb together with the nitrogen atom to which they are attached represent a saturated 3 to 7 membered heterocyclic ring optionally including an O, a group CONRcRd in which Rc and Rd independently represent H or a C1-4alkyl group or Rc and Rd together with the nitrogen atom to which they are attached represent a saturated 3 to 7 membered heterocyclic ring;
- n represents 0, 1, 2 or 3;
- R2 represents a C1-4alkyl group optionally substituted by one or more fluoro or a C1-4alkoxy group optionally substituted by one or more fluoro, a group NRaRb in which Ra and Rb independently represent H or a C1-4 alkyl group or Ra and Rb together with the nitrogen atom to which they are attached represent a saturated 3 to 7 membered heterocyclic ring optionally including an O, a group CONRcRd in which Rc and Rd independently represent H or a C1-4alkyl group or Rc and Rd together with the nitrogen atom to which they are attached represent a saturated 3 to 7 membered heterocyclic ring;
- m represents 0 or 1;
- R3 represents H or a C1-4 alkyl group;
- L1 represents a (CH2)pC3-10 cycloalkyl(CH2)q group in which p and q are independently selected from 0 and 1 and in which the cycloalkyl group may be monocyclic or bicyclic and optionally may be bridged provided that the two nitrogens bearing R3 and R4, respectively, are not linked to the same carbon atom, and wherein one of the carbons may be replaced by O or, alternatively, the group —N(R3)-L1- or the group L1-N(R4) together represent a saturated bicyclic heterocyclic ring containing from 2 to 9 carbon atoms and the nitrogen bearing R3 or R4 respectively;
- and
- R4 represents H or a C1-4 alkyl group optionally substituted by one or more of the following:
- fluoro or C1-4 alkoxy optionally substituted by one or more fluoro.
7 more elements
A compound selected from one or more of:
- (1S,3S)-Dibenzyl-cyclohexane-1,3-diylbiscarbamate;
- and
- (1S,3S)-Cyclohexane-1,3-diamine dihydrochloride.
Dependencies are inferred from the claim text.