CA1105938A - Cetals de 4-amino-4-arylcyclohexanones - Google Patents

Cetals de 4-amino-4-arylcyclohexanones

Info

Publication number: CA1105938A
Authority: CA; Canada
Prior art keywords: ethylene ketal; cyclohexanone; prepared; procedure; mole
Prior art date: 1976-06-03
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA359,623A

Other languages

English (en)

Inventor

Daniel Lednicer

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pharmacia and Upjohn Co

Original Assignee

Upjohn Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-06-03

Filing date

1980-09-05

Publication date

1981-07-28

1976-06-03 Priority claimed from US05/692,589 external-priority patent/US4065573A/en

1980-09-05 Application filed by Upjohn Co filed Critical Upjohn Co

1980-09-05 Priority to CA359,623A priority Critical patent/CA1105938A/fr

1981-07-28 Application granted granted Critical

1981-07-28 Publication of CA1105938A publication Critical patent/CA1105938A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 claims abstract description 220
150000001875 compounds Chemical class 0.000 claims abstract description 140
239000002253 acid Substances 0.000 claims abstract description 44
239000001257 hydrogen Substances 0.000 claims abstract description 16
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
230000008569 process Effects 0.000 claims abstract description 9
-1 inclusive Chemical group 0.000 claims description 107
125000004432 carbon atom Chemical group C* 0.000 claims description 59
125000000217 alkyl group Chemical group 0.000 claims description 33
239000003960 organic solvent Substances 0.000 claims description 17
239000000126 substance Substances 0.000 claims description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
239000007818 Grignard reagent Substances 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
150000004795 grignard reagents Chemical class 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
150000001412 amines Chemical class 0.000 claims description 6
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical group 0.000 claims description 6
239000012442 inert solvent Substances 0.000 claims description 3
150000002009 diols Chemical class 0.000 claims description 2
230000003647 oxidation Effects 0.000 claims description 2
238000007254 oxidation reaction Methods 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 138
150000003839 salts Chemical class 0.000 abstract description 36
230000000051 modifying effect Effects 0.000 abstract description 35
DZGRKWDNSUAKTG-UHFFFAOYSA-N 4-[butyl(methyl)amino]-4-(3-hydroxyphenyl)cyclohexan-1-one;ethene Chemical group C=C.C=1C=CC(O)=CC=1C1(N(C)CCCC)CCC(=O)CC1 DZGRKWDNSUAKTG-UHFFFAOYSA-N 0.000 abstract description 18
241001465754 Metazoa Species 0.000 abstract description 16
150000003840 hydrochlorides Chemical class 0.000 abstract description 15
230000000202 analgesic effect Effects 0.000 abstract description 13
239000002552 dosage form Substances 0.000 abstract description 12
208000002193 Pain Diseases 0.000 abstract description 11
230000015572 biosynthetic process Effects 0.000 abstract description 11
230000036407 pain Effects 0.000 abstract description 11
238000011282 treatment Methods 0.000 abstract description 11
230000000694 effects Effects 0.000 abstract description 10
238000003786 synthesis reaction Methods 0.000 abstract description 10
239000000730 antalgic agent Substances 0.000 abstract description 8
229940035676 analgesics Drugs 0.000 abstract description 7
239000003887 narcotic antagonist Substances 0.000 abstract description 6
230000001225 therapeutic effect Effects 0.000 abstract description 5
CMTICXBAFHOPCX-UHFFFAOYSA-N 4-(dimethylamino)-4-(3-hydroxyphenyl)cyclohexan-1-one;ethene Chemical group C=C.C=1C=CC(O)=CC=1C1(N(C)C)CCC(=O)CC1 CMTICXBAFHOPCX-UHFFFAOYSA-N 0.000 abstract description 4
230000000241 respiratory effect Effects 0.000 abstract description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
230000003542 behavioural effect Effects 0.000 abstract description 2
230000002526 effect on cardiovascular system Effects 0.000 abstract 1
239000005977 Ethylene Substances 0.000 description 384
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 382
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 322
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 271
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 266
238000002360 preparation method Methods 0.000 description 154
238000004458 analytical method Methods 0.000 description 143
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 142
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 135
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 127
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 126
238000002844 melting Methods 0.000 description 120
230000008018 melting Effects 0.000 description 120
239000000203 mixture Substances 0.000 description 116
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 109
239000000243 solution Substances 0.000 description 96
229940073584 methylene chloride Drugs 0.000 description 90
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 86
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 81
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 79
230000002829 reductive effect Effects 0.000 description 75
238000001704 evaporation Methods 0.000 description 73
230000008020 evaporation Effects 0.000 description 73
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 68
239000012458 free base Substances 0.000 description 66
230000000875 corresponding effect Effects 0.000 description 63
239000002904 solvent Substances 0.000 description 60
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 56
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 55
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 49
239000011541 reaction mixture Substances 0.000 description 49
229940076134 benzene Drugs 0.000 description 48
238000010992 reflux Methods 0.000 description 45
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 43
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
229940093499 ethyl acetate Drugs 0.000 description 42
235000019439 ethyl acetate Nutrition 0.000 description 42
239000007787 solid Substances 0.000 description 40
239000012267 brine Substances 0.000 description 39
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 39
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 38
239000013078 crystal Substances 0.000 description 35
235000002639 sodium chloride Nutrition 0.000 description 35
239000003921 oil Substances 0.000 description 33
235000019198 oils Nutrition 0.000 description 32
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
235000011167 hydrochloric acid Nutrition 0.000 description 30
229960000443 hydrochloric acid Drugs 0.000 description 30
239000002244 precipitate Substances 0.000 description 29
238000006243 chemical reaction Methods 0.000 description 28
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
GIPFCXTUXOTXRL-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-(dimethylamino)cyclohexan-1-one Chemical compound C=1C=C(Cl)C=CC=1C1(N(C)C)CCC(=O)CC1 GIPFCXTUXOTXRL-UHFFFAOYSA-N 0.000 description 26
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 26
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 26
238000007792 addition Methods 0.000 description 26
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 26
229910000041 hydrogen chloride Inorganic materials 0.000 description 26
238000001953 recrystallisation Methods 0.000 description 26
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 25
238000003756 stirring Methods 0.000 description 25
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 24
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 24
239000003826 tablet Substances 0.000 description 24
CLNXKPRXMYQSOL-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-oxocyclohexane-1-carbonitrile Chemical compound C1=CC(Cl)=CC=C1C1(C#N)CCC(=O)CC1 CLNXKPRXMYQSOL-UHFFFAOYSA-N 0.000 description 22
239000002775 capsule Substances 0.000 description 22
239000007788 liquid Substances 0.000 description 22
239000000741 silica gel Substances 0.000 description 22
229910002027 silica gel Inorganic materials 0.000 description 22
239000000725 suspension Substances 0.000 description 22
239000008187 granular material Substances 0.000 description 21
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 20
238000010438 heat treatment Methods 0.000 description 20
239000002243 precursor Substances 0.000 description 20
239000000460 chlorine Substances 0.000 description 19
229960000583 acetic acid Drugs 0.000 description 18
239000000706 filtrate Substances 0.000 description 18
HKLNGNRLBNQVOQ-UHFFFAOYSA-N 4-(dimethylamino)-4-(3-hydroxyphenyl)cyclohexan-1-one Chemical compound C=1C=CC(O)=CC=1C1(N(C)C)CCC(=O)CC1 HKLNGNRLBNQVOQ-UHFFFAOYSA-N 0.000 description 17
238000009835 boiling Methods 0.000 description 17
239000010410 layer Substances 0.000 description 17
239000012044 organic layer Substances 0.000 description 17
239000000047 product Substances 0.000 description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
239000012280 lithium aluminium hydride Substances 0.000 description 16
WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 16
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 14
229940086542 triethylamine Drugs 0.000 description 14
SXNDEPISTBXLDD-UHFFFAOYSA-N 4-[butyl(methyl)amino]-4-(3-hydroxyphenyl)cyclohexan-1-one Chemical compound C=1C=CC(O)=CC=1C1(N(C)CCCC)CCC(=O)CC1 SXNDEPISTBXLDD-UHFFFAOYSA-N 0.000 description 13
239000003085 diluting agent Substances 0.000 description 13
UAHBIGYKUJRYPQ-UHFFFAOYSA-N methyl 5-(4-chlorophenyl)-5-cyano-2-oxocyclohexane-1-carboxylate Chemical compound C1CC(=O)C(C(=O)OC)CC1(C#N)C1=CC=C(Cl)C=C1 UAHBIGYKUJRYPQ-UHFFFAOYSA-N 0.000 description 13
239000003208 petroleum Substances 0.000 description 13
229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
VZRMIGAKKALGQB-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-cyanoheptanedioic acid Chemical compound OC(=O)CCC(CCC(O)=O)(C#N)C1=CC=C(Cl)C=C1 VZRMIGAKKALGQB-UHFFFAOYSA-N 0.000 description 12
IVYMIRMKXZAHRV-UHFFFAOYSA-N 4-chlorophenylacetonitrile Chemical compound ClC1=CC=C(CC#N)C=C1 IVYMIRMKXZAHRV-UHFFFAOYSA-N 0.000 description 12
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 12
239000000538 analytical sample Substances 0.000 description 12
DCZFGQYXRKMVFG-UHFFFAOYSA-N cyclohexane-1,4-dione Chemical compound O=C1CCC(=O)CC1 DCZFGQYXRKMVFG-UHFFFAOYSA-N 0.000 description 12
239000000796 flavoring agent Substances 0.000 description 12
239000000463 material Substances 0.000 description 12
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 12
235000017557 sodium bicarbonate Nutrition 0.000 description 12
GZGPRZYZKBQPBQ-UHFFFAOYSA-N 1,4-dioxaspiro[4.5]decane Chemical compound O1CCOC11CCCCC1 GZGPRZYZKBQPBQ-UHFFFAOYSA-N 0.000 description 11
FKYDNMYCXJKDIR-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-oxocyclohexane-1-carboxylic acid Chemical compound C=1C=C(Cl)C=CC=1C1(C(=O)O)CCC(=O)CC1 FKYDNMYCXJKDIR-UHFFFAOYSA-N 0.000 description 11
VCEODKLEIJWHMI-UHFFFAOYSA-N 4-(dimethylamino)-4-(4-methylphenyl)cyclohexan-1-one Chemical compound C=1C=C(C)C=CC=1C1(N(C)C)CCC(=O)CC1 VCEODKLEIJWHMI-UHFFFAOYSA-N 0.000 description 11
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
239000000284 extract Substances 0.000 description 11
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 11
239000012279 sodium borohydride Substances 0.000 description 11
229910000033 sodium borohydride Inorganic materials 0.000 description 11
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 10
238000001816 cooling Methods 0.000 description 10
238000004821 distillation Methods 0.000 description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
239000000843 powder Substances 0.000 description 10
229940032330 sulfuric acid Drugs 0.000 description 10
AEMJVQKBEPXDTO-UHFFFAOYSA-N 4-(2-chlorophenyl)-4-(dimethylamino)cyclohexan-1-one Chemical compound C=1C=CC=C(Cl)C=1C1(N(C)C)CCC(=O)CC1 AEMJVQKBEPXDTO-UHFFFAOYSA-N 0.000 description 9
RKTHEORTILWEMB-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-isocyanatocyclohexan-1-one Chemical compound C1=CC(Cl)=CC=C1C1(N=C=O)CCC(=O)CC1 RKTHEORTILWEMB-UHFFFAOYSA-N 0.000 description 9
WRBREOAXTQDEJF-UHFFFAOYSA-N 4-(dimethylamino)-4-[(4-methoxyphenyl)methyl]cyclohexan-1-one Chemical compound C1=CC(OC)=CC=C1CC1(N(C)C)CCC(=O)CC1 WRBREOAXTQDEJF-UHFFFAOYSA-N 0.000 description 9
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 9
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
229930006000 Sucrose Natural products 0.000 description 9
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 9
239000003086 colorant Substances 0.000 description 9
239000000306 component Substances 0.000 description 9
239000000839 emulsion Substances 0.000 description 9
235000013355 food flavoring agent Nutrition 0.000 description 9
239000005720 sucrose Substances 0.000 description 9
239000003981 vehicle Substances 0.000 description 9
PPBCXLZCSMVSNY-UHFFFAOYSA-N 1-[(3-methoxyphenyl)methyl]-4-oxocyclohexane-1-carbonitrile Chemical compound COC1=CC=CC(CC2(CCC(=O)CC2)C#N)=C1 PPBCXLZCSMVSNY-UHFFFAOYSA-N 0.000 description 8
FUNZUWAJMVRIRL-UHFFFAOYSA-N 4-(4-bromophenyl)-4-(dimethylamino)cyclohexan-1-one Chemical compound C=1C=C(Br)C=CC=1C1(N(C)C)CCC(=O)CC1 FUNZUWAJMVRIRL-UHFFFAOYSA-N 0.000 description 8
AIGRYLPSZFFWAK-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-(methylamino)cyclohexan-1-one Chemical compound C=1C=C(Cl)C=CC=1C1(NC)CCC(=O)CC1 AIGRYLPSZFFWAK-UHFFFAOYSA-N 0.000 description 8
ULUPKLLIXIIQRH-UHFFFAOYSA-N 4-(dimethylamino)-4-(4-fluorophenyl)cyclohexan-1-one Chemical compound C=1C=C(F)C=CC=1C1(N(C)C)CCC(=O)CC1 ULUPKLLIXIIQRH-UHFFFAOYSA-N 0.000 description 8
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 8
239000008346 aqueous phase Substances 0.000 description 8
239000002585 base Substances 0.000 description 8
235000008504 concentrate Nutrition 0.000 description 8
239000012141 concentrate Substances 0.000 description 8
238000010828 elution Methods 0.000 description 8
230000000144 pharmacologic effect Effects 0.000 description 8
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 8
239000000080 wetting agent Substances 0.000 description 8
BHNGPNBNTPBTTQ-UHFFFAOYSA-N 1-(3-hydroxyphenyl)-4-oxocyclohexane-1-carbonitrile Chemical compound OC1=CC=CC(C2(CCC(=O)CC2)C#N)=C1 BHNGPNBNTPBTTQ-UHFFFAOYSA-N 0.000 description 7
NACNNOHDRLNBKW-UHFFFAOYSA-N 4-(dimethylamino)-4-[(3-methoxyphenyl)methyl]cyclohexan-1-one Chemical compound COC1=CC=CC(CC2(CCC(=O)CC2)N(C)C)=C1 NACNNOHDRLNBKW-UHFFFAOYSA-N 0.000 description 7
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 7
125000002947 alkylene group Chemical group 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 7
229910052799 carbon Inorganic materials 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
235000019441 ethanol Nutrition 0.000 description 7
239000004615 ingredient Substances 0.000 description 7
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 7
229910052753 mercury Inorganic materials 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
239000011734 sodium Substances 0.000 description 7
238000004809 thin layer chromatography Methods 0.000 description 7
AMKHTXBTVCCLPT-UHFFFAOYSA-N 1-(dimethylamino)-4-oxocyclohexane-1-carbonitrile Chemical compound CN(C)C1(C#N)CCC(=O)CC1 AMKHTXBTVCCLPT-UHFFFAOYSA-N 0.000 description 6
KVFVLGAOBMXUSH-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]-4-oxocyclohexane-1-carbonitrile Chemical compound C1=CC(OC)=CC=C1CC1(C#N)CCC(=O)CC1 KVFVLGAOBMXUSH-UHFFFAOYSA-N 0.000 description 6
RHBWOPOTHAKLHD-UHFFFAOYSA-N 1-[butyl(methyl)amino]-4-oxocyclohexane-1-carbonitrile Chemical compound CCCCN(C)C1(C#N)CCC(=O)CC1 RHBWOPOTHAKLHD-UHFFFAOYSA-N 0.000 description 6
DEOPEYZZVGZQFC-UHFFFAOYSA-N 4-(dimethylamino)-4-phenylcyclohexan-1-one Chemical compound C=1C=CC=CC=1C1(N(C)C)CCC(=O)CC1 DEOPEYZZVGZQFC-UHFFFAOYSA-N 0.000 description 6
OOHVPJGDPFGVNV-UHFFFAOYSA-N 4-(methylamino)-4-phenylcyclohexan-1-one Chemical compound C=1C=CC=CC=1C1(NC)CCC(=O)CC1 OOHVPJGDPFGVNV-UHFFFAOYSA-N 0.000 description 6
GKXOABVSZWCJJK-UHFFFAOYSA-N 4-oxo-1-phenylcyclohexane-1-carbonitrile Chemical compound C1CC(=O)CCC1(C#N)C1=CC=CC=C1 GKXOABVSZWCJJK-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 6
QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 6
239000011149 active material Substances 0.000 description 6
239000007891 compressed tablet Substances 0.000 description 6
125000006310 cycloalkyl amino group Chemical group 0.000 description 6
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
235000003599 food sweetener Nutrition 0.000 description 6
229920000159 gelatin Polymers 0.000 description 6
239000008273 gelatin Substances 0.000 description 6
239000012362 glacial acetic acid Substances 0.000 description 6
239000008101 lactose Substances 0.000 description 6
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 6
239000012071 phase Substances 0.000 description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
239000006215 rectal suppository Substances 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 6
235000015424 sodium Nutrition 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000000829 suppository Substances 0.000 description 6
239000003765 sweetening agent Substances 0.000 description 6
235000020357 syrup Nutrition 0.000 description 6
239000006188 syrup Substances 0.000 description 6
BIMOIQNSDSBDDZ-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-oxocyclohexane-1-carbonitrile Chemical compound ClC1=CC=CC=C1C1(C#N)CCC(=O)CC1 BIMOIQNSDSBDDZ-UHFFFAOYSA-N 0.000 description 5
YDVFTCZQEZJUIH-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-4-oxocyclohexane-1-carbonitrile Chemical compound C1=C(Cl)C(Cl)=CC=C1C1(C#N)CCC(=O)CC1 YDVFTCZQEZJUIH-UHFFFAOYSA-N 0.000 description 5
DGEFSVRXOCLHAY-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-4-oxocyclohexane-1-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1(C#N)CCC(=O)CC1 DGEFSVRXOCLHAY-UHFFFAOYSA-N 0.000 description 5
FNWWTNNFZGBMEM-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-oxocyclohexane-1-carbonitrile Chemical compound C1=CC(F)=CC=C1C1(C#N)CCC(=O)CC1 FNWWTNNFZGBMEM-UHFFFAOYSA-N 0.000 description 5
RYTSBLXGZFFBOQ-UHFFFAOYSA-N 1-(4-methylphenyl)-4-oxocyclohexane-1-carbonitrile Chemical compound C1=CC(C)=CC=C1C1(C#N)CCC(=O)CC1 RYTSBLXGZFFBOQ-UHFFFAOYSA-N 0.000 description 5
FWWGZNOEEQTBPT-UHFFFAOYSA-N 1-butyl-3-(methylamino)-4-oxocyclohexane-1-carbonitrile Chemical compound CCCCC1(C#N)CCC(=O)C(NC)C1 FWWGZNOEEQTBPT-UHFFFAOYSA-N 0.000 description 5
MNOJRWOWILAHAV-UHFFFAOYSA-N 3-bromophenol Chemical compound OC1=CC=CC(Br)=C1 MNOJRWOWILAHAV-UHFFFAOYSA-N 0.000 description 5
QUNDOBCBABUEOE-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-4-(dimethylamino)cyclohexan-1-one Chemical compound C=1C=C(Cl)C=C(Cl)C=1C1(N(C)C)CCC(=O)CC1 QUNDOBCBABUEOE-UHFFFAOYSA-N 0.000 description 5
HVKRFWCCSCENQC-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-4-(dimethylamino)cyclohexan-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C1(N(C)C)CCC(=O)CC1 HVKRFWCCSCENQC-UHFFFAOYSA-N 0.000 description 5
MWFVWRDGDVLNIJ-UHFFFAOYSA-N 4-(dimethylamino)-4-thiophen-2-ylcyclohexan-1-one Chemical compound C=1C=CSC=1C1(N(C)C)CCC(=O)CC1 MWFVWRDGDVLNIJ-UHFFFAOYSA-N 0.000 description 5
108010010803 Gelatin Proteins 0.000 description 5
206010019233 Headaches Diseases 0.000 description 5
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 5
125000004423 acyloxy group Chemical group 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
239000000499 gel Substances 0.000 description 5
235000019322 gelatine Nutrition 0.000 description 5
235000011852 gelatine desserts Nutrition 0.000 description 5
229940093915 gynecological organic acid Drugs 0.000 description 5
231100000869 headache Toxicity 0.000 description 5
239000007924 injection Substances 0.000 description 5
238000002347 injection Methods 0.000 description 5
229910052500 inorganic mineral Inorganic materials 0.000 description 5
239000012948 isocyanate Substances 0.000 description 5
150000002513 isocyanates Chemical class 0.000 description 5
229910052749 magnesium Inorganic materials 0.000 description 5
229940091250 magnesium supplement Drugs 0.000 description 5
235000010755 mineral Nutrition 0.000 description 5
239000011707 mineral Substances 0.000 description 5
150000007524 organic acids Chemical class 0.000 description 5
235000005985 organic acids Nutrition 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
238000001556 precipitation Methods 0.000 description 5
239000000454 talc Substances 0.000 description 5
229910052623 talc Inorganic materials 0.000 description 5
235000012222 talc Nutrition 0.000 description 5
238000005406 washing Methods 0.000 description 5
ALYQPOYEXMIQDZ-UHFFFAOYSA-N 1-(2-methylphenyl)-4-oxocyclohexane-1-carbonitrile Chemical compound CC1=CC=CC=C1C1(C#N)CCC(=O)CC1 ALYQPOYEXMIQDZ-UHFFFAOYSA-N 0.000 description 4
KTUMOHADVSXZNV-UHFFFAOYSA-N 1-(4-bromophenyl)-4-oxocyclohexane-1-carbonitrile Chemical compound C1=CC(Br)=CC=C1C1(C#N)CCC(=O)CC1 KTUMOHADVSXZNV-UHFFFAOYSA-N 0.000 description 4
HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 4
VKYFEMFNWHTVLX-UHFFFAOYSA-N 4-(3-hydroxyphenyl)-4-pyrrolidin-1-ylcyclohexan-1-one Chemical compound OC1=CC=CC(C2(CCC(=O)CC2)N2CCCC2)=C1 VKYFEMFNWHTVLX-UHFFFAOYSA-N 0.000 description 4
BGOUSBRBUNITCX-UHFFFAOYSA-N 4-(dimethylamino)-4-(2-methylphenyl)cyclohexan-1-one Chemical compound C=1C=CC=C(C)C=1C1(N(C)C)CCC(=O)CC1 BGOUSBRBUNITCX-UHFFFAOYSA-N 0.000 description 4
JRWPUXZIMODNJU-UHFFFAOYSA-N 4-(dimethylamino)-4-[4-(trifluoromethyl)phenyl]cyclohexan-1-one Chemical compound C=1C=C(C(F)(F)F)C=CC=1C1(N(C)C)CCC(=O)CC1 JRWPUXZIMODNJU-UHFFFAOYSA-N 0.000 description 4
JRJVHCQORVJEKJ-UHFFFAOYSA-N 4-[2-hydroxyethyl(methyl)amino]-4-phenylcyclohexan-1-one Chemical compound C=1C=CC=CC=1C1(N(CCO)C)CCC(=O)CC1 JRJVHCQORVJEKJ-UHFFFAOYSA-N 0.000 description 4
NMYKKHGVJOMOLM-UHFFFAOYSA-N 4-[butyl(methyl)amino]-4-(4-hydroxyphenyl)cyclohexan-1-one;ethene Chemical group C=C.C=1C=C(O)C=CC=1C1(N(C)CCCC)CCC(=O)CC1 NMYKKHGVJOMOLM-UHFFFAOYSA-N 0.000 description 4
JXNHEUAANNGFFV-UHFFFAOYSA-N 4-amino-4-phenylcyclohexan-1-one Chemical compound C=1C=CC=CC=1C1(N)CCC(=O)CC1 JXNHEUAANNGFFV-UHFFFAOYSA-N 0.000 description 4
PNIRSSRRQZFMDI-UHFFFAOYSA-N 4-cyano-4-(3,4-dimethoxyphenyl)heptanedioic acid Chemical compound COC1=CC=C(C(CCC(O)=O)(CCC(O)=O)C#N)C=C1OC PNIRSSRRQZFMDI-UHFFFAOYSA-N 0.000 description 4
ALRLCKXXSWRJQO-UHFFFAOYSA-N 4-oxo-1-thiophen-2-ylcyclohexane-1-carbonitrile Chemical compound C1CC(=O)CCC1(C#N)C1=CC=CS1 ALRLCKXXSWRJQO-UHFFFAOYSA-N 0.000 description 4
HBVUBDNRZWJTSB-UHFFFAOYSA-N 4-phenyl-4-piperidin-1-ylcyclohexan-1-one Chemical compound C1CC(=O)CCC1(C=1C=CC=CC=1)N1CCCCC1 HBVUBDNRZWJTSB-UHFFFAOYSA-N 0.000 description 4
JRXBINFSAFPOSX-UHFFFAOYSA-N 4-phenyl-4-pyrrolidin-1-ylcyclohexan-1-one Chemical compound C1CC(=O)CCC1(C=1C=CC=CC=1)N1CCCC1 JRXBINFSAFPOSX-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
241000416162 Astragalus gummifer Species 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
229920002261 Corn starch Polymers 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
229920001615 Tragacanth Polymers 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
235000019270 ammonium chloride Nutrition 0.000 description 4
229940073608 benzyl chloride Drugs 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
229960004424 carbon dioxide Drugs 0.000 description 4
229960004878 chlorphenesin carbamate Drugs 0.000 description 4
SKPLBLUECSEIFO-UHFFFAOYSA-N chlorphenesin carbamate Chemical compound NC(=O)OCC(O)COC1=CC=C(Cl)C=C1 SKPLBLUECSEIFO-UHFFFAOYSA-N 0.000 description 4
235000015165 citric acid Nutrition 0.000 description 4
OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 4
239000008120 corn starch Substances 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
230000003247 decreasing effect Effects 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000003814 drug Substances 0.000 description 4
239000003995 emulsifying agent Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
230000006870 function Effects 0.000 description 4
235000011187 glycerol Nutrition 0.000 description 4
230000001939 inductive effect Effects 0.000 description 4
230000002452 interceptive effect Effects 0.000 description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
235000001055 magnesium Nutrition 0.000 description 4
239000011777 magnesium Substances 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
239000006186 oral dosage form Substances 0.000 description 4
229960000482 pethidine Drugs 0.000 description 4
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 4
229920000053 polysorbate 80 Polymers 0.000 description 4
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 4
239000003755 preservative agent Substances 0.000 description 4
229960004063 propylene glycol Drugs 0.000 description 4
235000013772 propylene glycol Nutrition 0.000 description 4
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 4
239000000376 reactant Substances 0.000 description 4
238000000638 solvent extraction Methods 0.000 description 4
239000011877 solvent mixture Substances 0.000 description 4
239000008107 starch Substances 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
239000000375 suspending agent Substances 0.000 description 4
235000010487 tragacanth Nutrition 0.000 description 4
239000000196 tragacanth Substances 0.000 description 4
229940116362 tragacanth Drugs 0.000 description 4
239000001993 wax Substances 0.000 description 4
OUKRPSQXZBCMEC-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-4-oxocyclohexane-1-carbonitrile Chemical compound ClC1=CC(Cl)=CC=C1C1(C#N)CCC(=O)CC1 OUKRPSQXZBCMEC-UHFFFAOYSA-N 0.000 description 3
ZBDTUKWTMANXAU-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-oxocyclohexane-1-carboxylic acid Chemical compound C=1C=CC=C(Cl)C=1C1(C(=O)O)CCC(=O)CC1 ZBDTUKWTMANXAU-UHFFFAOYSA-N 0.000 description 3
YLJKQDCUVKTPEE-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-4-oxocyclohexane-1-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC=C1C1(C(O)=O)CCC(=O)CC1 YLJKQDCUVKTPEE-UHFFFAOYSA-N 0.000 description 3
PNHZFEULIUHIQX-UHFFFAOYSA-N 1-(3-chlorophenyl)-4-oxocyclohexane-1-carbonitrile Chemical compound ClC1=CC=CC(C2(CCC(=O)CC2)C#N)=C1 PNHZFEULIUHIQX-UHFFFAOYSA-N 0.000 description 3
IGJQKWIMCAZJCO-UHFFFAOYSA-N 1-(4-methylphenyl)-4-oxocyclohexane-1-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1(C(O)=O)CCC(=O)CC1 IGJQKWIMCAZJCO-UHFFFAOYSA-N 0.000 description 3
XCRFBPITQWORIY-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]-4-oxocyclohexane-1-carboxylic acid Chemical compound C1=CC(OC)=CC=C1CC1(C(O)=O)CCC(=O)CC1 XCRFBPITQWORIY-UHFFFAOYSA-N 0.000 description 3
GTKXUZSXGQXAQN-UHFFFAOYSA-N 4-(2-chlorophenyl)-4-(methylamino)cyclohexan-1-one Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCC(=O)CC1 GTKXUZSXGQXAQN-UHFFFAOYSA-N 0.000 description 3
IEEGPUDXXRHZBG-UHFFFAOYSA-N 4-(2-chlorophenyl)-4-isocyanatocyclohexan-1-one Chemical compound ClC1=CC=CC=C1C1(N=C=O)CCC(=O)CC1 IEEGPUDXXRHZBG-UHFFFAOYSA-N 0.000 description 3
LBJMSHMOGAFVLE-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-4-(dimethylamino)cyclohexan-1-one Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(N(C)C)CCC(=O)CC1 LBJMSHMOGAFVLE-UHFFFAOYSA-N 0.000 description 3
DRHQZMVLUIKRSB-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-4-(methylamino)cyclohexan-1-one Chemical compound C=1C=C(OC)C(OC)=CC=1C1(NC)CCC(=O)CC1 DRHQZMVLUIKRSB-UHFFFAOYSA-N 0.000 description 3
RYIXLNLJRGYTQM-UHFFFAOYSA-N 4-(3-chlorophenyl)-4-(dimethylamino)cyclohexan-1-one Chemical compound C=1C=CC(Cl)=CC=1C1(N(C)C)CCC(=O)CC1 RYIXLNLJRGYTQM-UHFFFAOYSA-N 0.000 description 3
ANOQGSNDAXUBQI-UHFFFAOYSA-N 4-(3-hydroxyphenyl)-4-[methyl(propyl)amino]cyclohexan-1-one Chemical compound C=1C=CC(O)=CC=1C1(N(C)CCC)CCC(=O)CC1 ANOQGSNDAXUBQI-UHFFFAOYSA-N 0.000 description 3
LLKRVHXYECUTCQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-(dimethylamino)cyclohexan-1-one;ethene Chemical group C=C.C=1C=C(Cl)C=CC=1C1(N(C)C)CCC(=O)CC1 LLKRVHXYECUTCQ-UHFFFAOYSA-N 0.000 description 3
FYZNUMSQUDBHSD-UHFFFAOYSA-N 4-(4-fluorophenyl)-4-(methylamino)cyclohexan-1-one Chemical compound C=1C=C(F)C=CC=1C1(NC)CCC(=O)CC1 FYZNUMSQUDBHSD-UHFFFAOYSA-N 0.000 description 3
PJWVAEMPDUWWJM-UHFFFAOYSA-N 4-(4-fluorophenyl)-4-isocyanatocyclohexan-1-one Chemical compound C1=CC(F)=CC=C1C1(N=C=O)CCC(=O)CC1 PJWVAEMPDUWWJM-UHFFFAOYSA-N 0.000 description 3
OWNSIJLYHWRVOA-UHFFFAOYSA-N 4-(4-tert-butylphenyl)-4-isocyanatocyclohexan-1-one;ethene Chemical group C=C.C1=CC(C(C)(C)C)=CC=C1C1(N=C=O)CCC(=O)CC1 OWNSIJLYHWRVOA-UHFFFAOYSA-N 0.000 description 3
YMNRYYJKTPTFFI-UHFFFAOYSA-N 4-(dimethylamino)-4-(3-methylphenyl)cyclohexan-1-one;ethene Chemical group C=C.C=1C=CC(C)=CC=1C1(N(C)C)CCC(=O)CC1 YMNRYYJKTPTFFI-UHFFFAOYSA-N 0.000 description 3
HFMAZPUYQUFUBG-UHFFFAOYSA-N 4-(methylamino)-4-thiophen-2-ylcyclohexan-1-one Chemical compound C=1C=CSC=1C1(NC)CCC(=O)CC1 HFMAZPUYQUFUBG-UHFFFAOYSA-N 0.000 description 3
XXFFLYVOHUQPML-UHFFFAOYSA-N 4-[(4-methoxyphenyl)methyl]-4-(methylamino)cyclohexan-1-one Chemical compound C=1C=C(OC)C=CC=1CC1(NC)CCC(=O)CC1 XXFFLYVOHUQPML-UHFFFAOYSA-N 0.000 description 3
WQIVROULPPNYEZ-UHFFFAOYSA-N 4-[butyl(methyl)amino]-4-(4-hydroxyphenyl)cyclohexan-1-one Chemical group C=1C=C(O)C=CC=1C1(N(C)CCCC)CCC(=O)CC1 WQIVROULPPNYEZ-UHFFFAOYSA-N 0.000 description 3
JFWJLYKWKXZSTB-UHFFFAOYSA-N 4-butyl-4-(3-hydroxyphenyl)-2-(methylamino)cyclohexan-1-one Chemical compound C=1C=CC(O)=CC=1C1(CCCC)CCC(=O)C(NC)C1 JFWJLYKWKXZSTB-UHFFFAOYSA-N 0.000 description 3
KWVWQSWPBYWZFE-UHFFFAOYSA-N 4-cyano-4-(2-methylphenyl)heptanedioic acid Chemical compound CC1=CC=CC=C1C(CCC(O)=O)(CCC(O)=O)C#N KWVWQSWPBYWZFE-UHFFFAOYSA-N 0.000 description 3
IYHDOSICIDXNRI-UHFFFAOYSA-N 4-cyano-4-(4-methylphenyl)heptanedioic acid Chemical compound CC1=CC=C(C(CCC(O)=O)(CCC(O)=O)C#N)C=C1 IYHDOSICIDXNRI-UHFFFAOYSA-N 0.000 description 3
PVKNVEFPJGEJAN-UHFFFAOYSA-N 4-cyano-4-[(3-methoxyphenyl)methyl]heptanedioic acid Chemical compound COC1=CC=CC(CC(CCC(O)=O)(CCC(O)=O)C#N)=C1 PVKNVEFPJGEJAN-UHFFFAOYSA-N 0.000 description 3
AGEGSTIGHJERIM-UHFFFAOYSA-N 4-cyano-4-[(4-methoxyphenyl)methyl]heptanedioic acid Chemical compound COC1=CC=C(CC(CCC(O)=O)(CCC(O)=O)C#N)C=C1 AGEGSTIGHJERIM-UHFFFAOYSA-N 0.000 description 3
GGMMIMNCDHPFQT-UHFFFAOYSA-N 4-cyano-4-phenylheptanedioic acid Chemical compound OC(=O)CCC(CCC(O)=O)(C#N)C1=CC=CC=C1 GGMMIMNCDHPFQT-UHFFFAOYSA-N 0.000 description 3
JADMUQXALNSOPB-UHFFFAOYSA-N 4-oxo-1-(3-phenylmethoxyphenyl)cyclohexane-1-carbonitrile Chemical compound C1CC(=O)CCC1(C#N)C1=CC=CC(OCC=2C=CC=CC=2)=C1 JADMUQXALNSOPB-UHFFFAOYSA-N 0.000 description 3
QCBZUMHZMKZEPH-UHFFFAOYSA-N 4-oxo-1-(3-phenylmethoxyphenyl)cyclohexane-1-carboxylic acid Chemical compound C=1C=CC(OCC=2C=CC=CC=2)=CC=1C1(C(=O)O)CCC(=O)CC1 QCBZUMHZMKZEPH-UHFFFAOYSA-N 0.000 description 3
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
239000005711 Benzoic acid Substances 0.000 description 3
ROTNBWYHUAGROV-UHFFFAOYSA-N C=C.C=1C=CC(O)=CC=1C1(NCCCCC)CCC(=O)CC1 Chemical group C=C.C=1C=CC(O)=CC=1C1(NCCCCC)CCC(=O)CC1 ROTNBWYHUAGROV-UHFFFAOYSA-N 0.000 description 3
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 3
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
235000010643 Leucaena leucocephala Nutrition 0.000 description 3
240000007472 Leucaena leucocephala Species 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
230000009471 action Effects 0.000 description 3
230000036592 analgesia Effects 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
235000010233 benzoic acid Nutrition 0.000 description 3
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
239000001768 carboxy methyl cellulose Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 3
239000000975 dye Substances 0.000 description 3
MKOAQOBBUDZZPQ-UHFFFAOYSA-N ethene;4-(3-hydroxyphenyl)-4-[methyl(pentyl)amino]cyclohexan-1-one Chemical group C=C.C=1C=CC(O)=CC=1C1(N(C)CCCCC)CCC(=O)CC1 MKOAQOBBUDZZPQ-UHFFFAOYSA-N 0.000 description 3
XTQQCOJOFZBFFU-UHFFFAOYSA-N ethene;4-(methylamino)-4-thiophen-2-ylcyclohexan-1-one Chemical group C=C.C=1C=CSC=1C1(NC)CCC(=O)CC1 XTQQCOJOFZBFFU-UHFFFAOYSA-N 0.000 description 3
XUBZMWJCNQQUPW-UHFFFAOYSA-N ethene;4-[ethyl(methyl)amino]-4-(3-phenylmethoxyphenyl)cyclohexan-1-one Chemical group C=C.C=1C=CC(OCC=2C=CC=CC=2)=CC=1C1(N(C)CC)CCC(=O)CC1 XUBZMWJCNQQUPW-UHFFFAOYSA-N 0.000 description 3
GMBJEOBPZNHHOR-UHFFFAOYSA-N ethene;4-isocyanato-4-(3-methylphenyl)cyclohexan-1-one Chemical group C=C.CC1=CC=CC(C2(CCC(=O)CC2)N=C=O)=C1 GMBJEOBPZNHHOR-UHFFFAOYSA-N 0.000 description 3
IOYGPWTVFDCZPA-UHFFFAOYSA-N ethene;ethyl n-(4-oxo-1-thiophen-2-ylcyclohexyl)carbamate Chemical group C=C.C=1C=CSC=1C1(NC(=O)OCC)CCC(=O)CC1 IOYGPWTVFDCZPA-UHFFFAOYSA-N 0.000 description 3
239000012259 ether extract Substances 0.000 description 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
235000019634 flavors Nutrition 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000007903 gelatin capsule Substances 0.000 description 3
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
238000007327 hydrogenolysis reaction Methods 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 3
239000000155 melt Substances 0.000 description 3
JNUNIHDBRZOUMB-UHFFFAOYSA-N methyl 5-cyano-2-oxo-5-phenylcyclohexane-1-carboxylate Chemical compound C1CC(=O)C(C(=O)OC)CC1(C#N)C1=CC=CC=C1 JNUNIHDBRZOUMB-UHFFFAOYSA-N 0.000 description 3
DQWYARSHPNEWHG-UHFFFAOYSA-N methyl 5-cyano-5-(2-methylphenyl)-2-oxocyclohexane-1-carboxylate Chemical compound C1CC(=O)C(C(=O)OC)CC1(C#N)C1=CC=CC=C1C DQWYARSHPNEWHG-UHFFFAOYSA-N 0.000 description 3
QXYHJWBBYNDQIL-UHFFFAOYSA-N methyl 5-cyano-5-(4-fluorophenyl)-2-oxocyclohexane-1-carboxylate Chemical compound C1CC(=O)C(C(=O)OC)CC1(C#N)C1=CC=C(F)C=C1 QXYHJWBBYNDQIL-UHFFFAOYSA-N 0.000 description 3
BPIAXJUVIKSBTH-UHFFFAOYSA-N methyl 5-cyano-5-(4-methylphenyl)-2-oxocyclohexane-1-carboxylate Chemical compound C1CC(=O)C(C(=O)OC)CC1(C#N)C1=CC=C(C)C=C1 BPIAXJUVIKSBTH-UHFFFAOYSA-N 0.000 description 3
OPTRQOHSVFVZSU-UHFFFAOYSA-N methyl 5-cyano-5-[(3-methoxyphenyl)methyl]-2-oxocyclohexane-1-carboxylate Chemical compound C1CC(=O)C(C(=O)OC)CC1(C#N)CC1=CC=CC(OC)=C1 OPTRQOHSVFVZSU-UHFFFAOYSA-N 0.000 description 3
ASXQWGHUIBROBT-UHFFFAOYSA-N methyl 5-cyano-5-[(4-methoxyphenyl)methyl]-2-oxocyclohexane-1-carboxylate Chemical compound C1CC(=O)C(C(=O)OC)CC1(C#N)CC1=CC=C(OC)C=C1 ASXQWGHUIBROBT-UHFFFAOYSA-N 0.000 description 3
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
229960005181 morphine Drugs 0.000 description 3
230000003533 narcotic effect Effects 0.000 description 3
LXCFILQKKLGQFO-UHFFFAOYSA-N p-hydroxybenzoic acid methyl ester Natural products COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 3
238000007911 parenteral administration Methods 0.000 description 3
WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 3
229940057838 polyethylene glycol 4000 Drugs 0.000 description 3
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
230000002035 prolonged effect Effects 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
238000000746 purification Methods 0.000 description 3
230000009467 reduction Effects 0.000 description 3
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 3
229940081974 saccharin Drugs 0.000 description 3
235000019204 saccharin Nutrition 0.000 description 3
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
WMGVPDQNPUQRND-UHFFFAOYSA-N (2-methylphenyl)acetonitrile Chemical compound CC1=CC=CC=C1CC#N WMGVPDQNPUQRND-UHFFFAOYSA-N 0.000 description 2
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 2
ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 2
HKQTYQDNCKMNHZ-UHFFFAOYSA-N 1,4-dioxaspiro[4.5]decan-8-ol Chemical compound C1CC(O)CCC21OCCO2 HKQTYQDNCKMNHZ-UHFFFAOYSA-N 0.000 description 2
VKRKCBWIVLSRBJ-UHFFFAOYSA-N 1,4-dioxaspiro[4.5]decan-8-one Chemical compound C1CC(=O)CCC21OCCO2 VKRKCBWIVLSRBJ-UHFFFAOYSA-N 0.000 description 2
RTHQIXYCYJHTTI-UHFFFAOYSA-N 1-(3-chlorophenyl)-4-oxocyclohexane-1-carboxylic acid Chemical compound C=1C=CC(Cl)=CC=1C1(C(=O)O)CCC(=O)CC1 RTHQIXYCYJHTTI-UHFFFAOYSA-N 0.000 description 2
HLQYZWCMJDKGRW-UHFFFAOYSA-N 1-(4-bromophenyl)-4-oxocyclohexane-1-carboxylic acid Chemical compound C=1C=C(Br)C=CC=1C1(C(=O)O)CCC(=O)CC1 HLQYZWCMJDKGRW-UHFFFAOYSA-N 0.000 description 2
UFZDFJOKZAATTD-UHFFFAOYSA-N 1-[(3-methoxyphenyl)methyl]-4-oxocyclohexane-1-carboxylic acid Chemical compound COC1=CC=CC(CC2(CCC(=O)CC2)C(O)=O)=C1 UFZDFJOKZAATTD-UHFFFAOYSA-N 0.000 description 2
BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 2
NNMBNYHMJRJUBC-UHFFFAOYSA-N 1-bromo-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(Br)=C1 NNMBNYHMJRJUBC-UHFFFAOYSA-N 0.000 description 2
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
ASLSUMISAQDOOB-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)acetonitrile Chemical compound COC1=CC=C(CC#N)C=C1OC ASLSUMISAQDOOB-UHFFFAOYSA-N 0.000 description 2
QKJPXROEIJPNHG-UHFFFAOYSA-N 2-(4-tert-butylphenyl)acetonitrile Chemical compound CC(C)(C)C1=CC=C(CC#N)C=C1 QKJPXROEIJPNHG-UHFFFAOYSA-N 0.000 description 2
JOZKRRZOWRUDEK-UHFFFAOYSA-N 2-(dimethylamino)cyclohexan-1-one Chemical compound CN(C)C1CCCCC1=O JOZKRRZOWRUDEK-UHFFFAOYSA-N 0.000 description 2
FKOKUHFZNIUSLW-UHFFFAOYSA-N 2-Hydroxypropyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(C)O FKOKUHFZNIUSLW-UHFFFAOYSA-N 0.000 description 2
QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
JZRPIWGJKSGDBJ-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-4-isocyanatocyclohexan-1-one Chemical compound ClC1=CC(Cl)=CC=C1C1(N=C=O)CCC(=O)CC1 JZRPIWGJKSGDBJ-UHFFFAOYSA-N 0.000 description 2
PYSSBCJBBHRBPS-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-4-(methylamino)cyclohexan-1-one Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(NC)CCC(=O)CC1 PYSSBCJBBHRBPS-UHFFFAOYSA-N 0.000 description 2
MUMGHHFONFJCQY-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-4-isocyanatocyclohexan-1-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1(N=C=O)CCC(=O)CC1 MUMGHHFONFJCQY-UHFFFAOYSA-N 0.000 description 2
XVSSFJTVYNGHIZ-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-4-isocyanatocyclohexan-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C1(N=C=O)CCC(=O)CC1 XVSSFJTVYNGHIZ-UHFFFAOYSA-N 0.000 description 2
OKCVQHKFDIBVSW-UHFFFAOYSA-N 4-(3-chlorophenyl)-4-cyanoheptanedioic acid Chemical compound OC(=O)CCC(CCC(O)=O)(C#N)C1=CC=CC(Cl)=C1 OKCVQHKFDIBVSW-UHFFFAOYSA-N 0.000 description 2
FXSZCFIBQLPSNZ-UHFFFAOYSA-N 4-(3-hydroxyphenyl)-4-[methyl(pentyl)amino]cyclohexan-1-one Chemical compound C=1C=CC(O)=CC=1C1(N(C)CCCCC)CCC(=O)CC1 FXSZCFIBQLPSNZ-UHFFFAOYSA-N 0.000 description 2
LOQVPAYSPARPDX-UHFFFAOYSA-N 4-(4-bromophenyl)-4-cyanoheptanedioic acid Chemical compound OC(=O)CCC(CCC(O)=O)(C#N)C1=CC=C(Br)C=C1 LOQVPAYSPARPDX-UHFFFAOYSA-N 0.000 description 2
KPIRKKGJHXZZNB-UHFFFAOYSA-N 4-(4-bromophenyl)-4-isocyanatocyclohexan-1-one Chemical compound C1=CC(Br)=CC=C1C1(N=C=O)CCC(=O)CC1 KPIRKKGJHXZZNB-UHFFFAOYSA-N 0.000 description 2
VMKXPXUMYQUBDW-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-(dimethylamino)-2-methylcyclohexan-1-one Chemical compound C1CC(=O)C(C)CC1(N(C)C)C1=CC=C(Cl)C=C1 VMKXPXUMYQUBDW-UHFFFAOYSA-N 0.000 description 2
JNBOVWFOTNYTES-UHFFFAOYSA-N 4-(4-chlorophenyl)cyclohexan-1-one Chemical compound C1=CC(Cl)=CC=C1C1CCC(=O)CC1 JNBOVWFOTNYTES-UHFFFAOYSA-N 0.000 description 2
MFLCLMNDELQEIH-UHFFFAOYSA-N 4-(4-tert-butylphenyl)-4-(dimethylamino)cyclohexan-1-one;ethene Chemical group C=C.C=1C=C(C(C)(C)C)C=CC=1C1(N(C)C)CCC(=O)CC1 MFLCLMNDELQEIH-UHFFFAOYSA-N 0.000 description 2
LJNSAVCUSKEQCF-UHFFFAOYSA-N 4-(dimethylamino)-2-methyl-4-(4-methylphenyl)cyclohexan-1-one Chemical compound C1CC(=O)C(C)CC1(N(C)C)C1=CC=C(C)C=C1 LJNSAVCUSKEQCF-UHFFFAOYSA-N 0.000 description 2
UJGRPCZQYSYZLQ-UHFFFAOYSA-N 4-(dimethylamino)-4-(3-hydroxy-4-methylphenyl)cyclohexan-1-one;ethene Chemical group C=C.C=1C=C(C)C(O)=CC=1C1(N(C)C)CCC(=O)CC1 UJGRPCZQYSYZLQ-UHFFFAOYSA-N 0.000 description 2
IBUHDMOTKGIYGA-UHFFFAOYSA-N 4-(dimethylamino)-4-(3-methylphenyl)cyclohexan-1-one Chemical group C=1C=CC(C)=CC=1C1(N(C)C)CCC(=O)CC1 IBUHDMOTKGIYGA-UHFFFAOYSA-N 0.000 description 2
SZBRQVYWYKGOOQ-UHFFFAOYSA-N 4-(dimethylamino)-4-(3-methylphenyl)cyclohexan-1-one;hydroiodide Chemical compound I.C=1C=CC(C)=CC=1C1(N(C)C)CCC(=O)CC1 SZBRQVYWYKGOOQ-UHFFFAOYSA-N 0.000 description 2
IVVBFTPNLVGJOO-UHFFFAOYSA-N 4-(methylamino)-4-(2-methylphenyl)cyclohexan-1-one Chemical compound C=1C=CC=C(C)C=1C1(NC)CCC(=O)CC1 IVVBFTPNLVGJOO-UHFFFAOYSA-N 0.000 description 2
XZJKHSRRQGEUFG-UHFFFAOYSA-N 4-(methylamino)-4-(3-phenylmethoxyphenyl)cyclohexan-1-one Chemical compound C=1C=CC(OCC=2C=CC=CC=2)=CC=1C1(NC)CCC(=O)CC1 XZJKHSRRQGEUFG-UHFFFAOYSA-N 0.000 description 2
QHRXLQGRCIHUSO-UHFFFAOYSA-N 4-(methylamino)-4-(4-methylphenyl)cyclohexan-1-one Chemical compound C=1C=C(C)C=CC=1C1(NC)CCC(=O)CC1 QHRXLQGRCIHUSO-UHFFFAOYSA-N 0.000 description 2
IKKMACDXHBWJFS-UHFFFAOYSA-N 4-(methylamino)-4-phenylcyclohexan-1-one;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C1(NC)CCC(=O)CC1 IKKMACDXHBWJFS-UHFFFAOYSA-N 0.000 description 2
KJIMZXWXSLVBEO-UHFFFAOYSA-N 4-(methylamino)cyclohexan-1-one Chemical compound CNC1CCC(=O)CC1 KJIMZXWXSLVBEO-UHFFFAOYSA-N 0.000 description 2
KYDKOJVTKVVYRB-UHFFFAOYSA-N 4-[(3-methoxyphenyl)methyl]-4-(methylamino)cyclohexan-1-one Chemical compound C=1C=CC(OC)=CC=1CC1(NC)CCC(=O)CC1 KYDKOJVTKVVYRB-UHFFFAOYSA-N 0.000 description 2
WHXMNTJJYWYCAK-UHFFFAOYSA-N 4-[butyl(ethyl)amino]-4-(3-hydroxyphenyl)cyclohexan-1-one Chemical compound C=1C=CC(O)=CC=1C1(N(CC)CCCC)CCC(=O)CC1 WHXMNTJJYWYCAK-UHFFFAOYSA-N 0.000 description 2
YZVBYXXFLWAXAW-UHFFFAOYSA-N 4-[butyl(methyl)amino]-4-(3-phenylmethoxyphenyl)cyclohexan-1-one;ethene Chemical group C=C.C=1C=CC(OCC=2C=CC=CC=2)=CC=1C1(N(C)CCCC)CCC(=O)CC1 YZVBYXXFLWAXAW-UHFFFAOYSA-N 0.000 description 2
PMTNZHVKVIIEIQ-UHFFFAOYSA-N 4-[butyl(methyl)amino]-4-(4-phenylmethoxyphenyl)cyclohexan-1-one;ethene Chemical group C=C.C=1C=C(OCC=2C=CC=CC=2)C=CC=1C1(N(C)CCCC)CCC(=O)CC1 PMTNZHVKVIIEIQ-UHFFFAOYSA-N 0.000 description 2
OLHDYTLPMOJBCE-UHFFFAOYSA-N 4-[cyclopropyl(methyl)amino]-4-(3-hydroxyphenyl)cyclohexan-1-one Chemical compound C1CC(=O)CCC1(C=1C=C(O)C=CC=1)N(C)C1CC1 OLHDYTLPMOJBCE-UHFFFAOYSA-N 0.000 description 2
RLAMTKCQYQANFQ-UHFFFAOYSA-N 4-[cyclopropylmethyl(methyl)amino]-4-(3-hydroxyphenyl)cyclohexan-1-one Chemical compound C1CC(=O)CCC1(C=1C=C(O)C=CC=1)N(C)CC1CC1 RLAMTKCQYQANFQ-UHFFFAOYSA-N 0.000 description 2
FCSVIPPQYQVVKJ-UHFFFAOYSA-N 4-amino-4-phenylcyclohexan-1-one;ethene Chemical group C=C.C=1C=CC=CC=1C1(N)CCC(=O)CC1 FCSVIPPQYQVVKJ-UHFFFAOYSA-N 0.000 description 2
VNZHRMJWKRZACH-UHFFFAOYSA-N 4-cyano-4-(2,4-dichlorophenyl)heptanedioic acid Chemical compound OC(=O)CCC(CCC(O)=O)(C#N)C1=CC=C(Cl)C=C1Cl VNZHRMJWKRZACH-UHFFFAOYSA-N 0.000 description 2
FBEFHEYRENJMCY-UHFFFAOYSA-N 4-cyano-4-(3,4-dichlorophenyl)heptanedioic acid Chemical compound OC(=O)CCC(CCC(O)=O)(C#N)C1=CC=C(Cl)C(Cl)=C1 FBEFHEYRENJMCY-UHFFFAOYSA-N 0.000 description 2
QMSXTDJYGAEOSX-UHFFFAOYSA-N 4-cyano-4-(4-fluorophenyl)heptanedioic acid Chemical compound OC(=O)CCC(CCC(O)=O)(C#N)C1=CC=C(F)C=C1 QMSXTDJYGAEOSX-UHFFFAOYSA-N 0.000 description 2
PTTJARMASQIQBC-UHFFFAOYSA-N 4-isocyanato-4-(2-methylphenyl)cyclohexan-1-one Chemical compound CC1=CC=CC=C1C1(N=C=O)CCC(=O)CC1 PTTJARMASQIQBC-UHFFFAOYSA-N 0.000 description 2
PQSBNPWKEYZNQN-UHFFFAOYSA-N 4-isocyanato-4-(4-methylphenyl)cyclohexan-1-one Chemical compound C1=CC(C)=CC=C1C1(N=C=O)CCC(=O)CC1 PQSBNPWKEYZNQN-UHFFFAOYSA-N 0.000 description 2
BYNQTKRJMKCXOL-UHFFFAOYSA-N 4-isocyanato-4-[(3-methoxyphenyl)methyl]cyclohexan-1-one Chemical compound COC1=CC=CC(CC2(CCC(=O)CC2)N=C=O)=C1 BYNQTKRJMKCXOL-UHFFFAOYSA-N 0.000 description 2
HLLXOJYHEJRGKC-UHFFFAOYSA-N 4-isocyanato-4-[(4-methoxyphenyl)methyl]cyclohexan-1-one Chemical compound C1=CC(OC)=CC=C1CC1(N=C=O)CCC(=O)CC1 HLLXOJYHEJRGKC-UHFFFAOYSA-N 0.000 description 2
LHCWKKDUHZLPFA-UHFFFAOYSA-N 4-isocyanato-4-phenylcyclohexan-1-one Chemical compound C=1C=CC=CC=1C1(N=C=O)CCC(=O)CC1 LHCWKKDUHZLPFA-UHFFFAOYSA-N 0.000 description 2
GLXVJOPRMXBHSI-UHFFFAOYSA-N 4-oxo-1-phenylcyclohexane-1-carboxylic acid Chemical compound C=1C=CC=CC=1C1(C(=O)O)CCC(=O)CC1 GLXVJOPRMXBHSI-UHFFFAOYSA-N 0.000 description 2
KUCDSAKHNGXHMG-UHFFFAOYSA-N 4-oxo-1-thiophen-2-ylcyclohexane-1-carboxylic acid Chemical compound C=1C=CSC=1C1(C(=O)O)CCC(=O)CC1 KUCDSAKHNGXHMG-UHFFFAOYSA-N 0.000 description 2
PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 2
ADDCVOVTPBVIOZ-UHFFFAOYSA-N 8-(dimethylamino)-1,4-dioxaspiro[4.5]decane-8-carbonitrile Chemical compound C1CC(N(C)C)(C#N)CCC21OCCO2 ADDCVOVTPBVIOZ-UHFFFAOYSA-N 0.000 description 2
YJZBIZUHEJXCGJ-UHFFFAOYSA-N 8-isocyanato-8-phenyl-1,4-dioxaspiro[4.5]decane Chemical compound C1CC(N=C=O)(C=2C=CC=CC=2)CCC21OCCO2 YJZBIZUHEJXCGJ-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
DMHSIPRFJFQGLF-UHFFFAOYSA-N C=C.OC1=CC=CC(C2CCC(=O)CC2)=C1 Chemical group C=C.OC1=CC=CC(C2CCC(=O)CC2)=C1 DMHSIPRFJFQGLF-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
241000241973 Cryptomyces maximus Species 0.000 description 2
UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
241000237858 Gastropoda Species 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
235000019501 Lemon oil Nutrition 0.000 description 2
229930195725 Mannitol Natural products 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
239000004264 Petrolatum Substances 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000008156 Ringer's lactate solution Substances 0.000 description 2
208000036366 Sensation of pressure Diseases 0.000 description 2
229920001800 Shellac Polymers 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
235000021355 Stearic acid Nutrition 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
JJFZTYMTEGCFJS-UHFFFAOYSA-N [3-(4-oxo-1-pyrrolidin-1-ylcyclohexyl)phenyl] acetate Chemical compound CC(=O)OC1=CC=CC(C2(CCC(=O)CC2)N2CCCC2)=C1 JJFZTYMTEGCFJS-UHFFFAOYSA-N 0.000 description 2
BQMMUUSDKOAIAX-UHFFFAOYSA-N [3-[1-(dimethylamino)-4-oxocyclohexyl]phenyl] acetate Chemical compound C=1C=CC(OC(C)=O)=CC=1C1(N(C)C)CCC(=O)CC1 BQMMUUSDKOAIAX-UHFFFAOYSA-N 0.000 description 2
PTJRRYLVJWTMIZ-UHFFFAOYSA-N [3-[1-[butyl(methyl)amino]-4-oxocyclohexyl]phenyl] acetate Chemical compound C=1C=CC(OC(C)=O)=CC=1C1(N(C)CCCC)CCC(=O)CC1 PTJRRYLVJWTMIZ-UHFFFAOYSA-N 0.000 description 2
RGUJYDJWTFAGHY-UHFFFAOYSA-N [3-[1-[methyl(pentyl)amino]-4-oxocyclohexyl]phenyl] acetate Chemical compound C=1C=CC(OC(C)=O)=CC=1C1(N(C)CCCCC)CCC(=O)CC1 RGUJYDJWTFAGHY-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical group CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
229960001138 acetylsalicylic acid Drugs 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000003708 ampul Substances 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
239000004599 antimicrobial Substances 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
239000008135 aqueous vehicle Substances 0.000 description 2
239000008122 artificial sweetener Substances 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
235000013871 bee wax Nutrition 0.000 description 2
239000012166 beeswax Substances 0.000 description 2
239000000440 bentonite Substances 0.000 description 2
235000012216 bentonite Nutrition 0.000 description 2
229910000278 bentonite Inorganic materials 0.000 description 2
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
239000000872 buffer Substances 0.000 description 2
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical group CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
235000013539 calcium stearate Nutrition 0.000 description 2
239000008116 calcium stearate Substances 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
239000004203 carnauba wax Substances 0.000 description 2
235000013869 carnauba wax Nutrition 0.000 description 2
210000003169 central nervous system Anatomy 0.000 description 2
239000002738 chelating agent Substances 0.000 description 2
239000007910 chewable tablet Substances 0.000 description 2
229960004126 codeine Drugs 0.000 description 2
235000012343 cottonseed oil Nutrition 0.000 description 2
239000002385 cottonseed oil Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 description 2
ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 2
239000008121 dextrose Substances 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
229940043279 diisopropylamine Drugs 0.000 description 2
CHIFJRILSUHVLI-UHFFFAOYSA-N dimethyl 4-cyano-4-thiophen-2-ylheptanedioate Chemical compound COC(=O)CCC(CCC(=O)OC)(C#N)C1=CC=CS1 CHIFJRILSUHVLI-UHFFFAOYSA-N 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
239000008298 dragée Substances 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
235000013399 edible fruits Nutrition 0.000 description 2
238000009505 enteric coating Methods 0.000 description 2
239000002702 enteric coating Substances 0.000 description 2
YJVSFBCARBMPFV-UHFFFAOYSA-N ethene;4-(methylamino)-4-(3-methylphenyl)cyclohexan-1-one Chemical group C=C.C=1C=CC(C)=CC=1C1(NC)CCC(=O)CC1 YJVSFBCARBMPFV-UHFFFAOYSA-N 0.000 description 2
TUSUIGFQOFNLMG-UHFFFAOYSA-N ethene;4-(methylamino)-4-(4-phenylmethoxyphenyl)cyclohexan-1-one Chemical group C=C.C=1C=C(OCC=2C=CC=CC=2)C=CC=1C1(NC)CCC(=O)CC1 TUSUIGFQOFNLMG-UHFFFAOYSA-N 0.000 description 2
ZNZITIGGLZFORQ-UHFFFAOYSA-N ethene;4-phenyl-4-pyrrolidin-1-ylcyclohexan-1-one Chemical group C=C.C1CC(=O)CCC1(C=1C=CC=CC=1)N1CCCC1 ZNZITIGGLZFORQ-UHFFFAOYSA-N 0.000 description 2
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 2
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000003925 fat Substances 0.000 description 2
235000019197 fats Nutrition 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
239000005457 ice water Substances 0.000 description 2
230000001965 increasing effect Effects 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
238000003780 insertion Methods 0.000 description 2
230000037431 insertion Effects 0.000 description 2
238000001361 intraarterial administration Methods 0.000 description 2
238000007918 intramuscular administration Methods 0.000 description 2
239000010501 lemon oil Substances 0.000 description 2
239000008297 liquid dosage form Substances 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
239000003589 local anesthetic agent Substances 0.000 description 2
229960005015 local anesthetics Drugs 0.000 description 2
239000007937 lozenge Substances 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
239000000594 mannitol Substances 0.000 description 2
235000010355 mannitol Nutrition 0.000 description 2
GISBVGIZKAWADG-UHFFFAOYSA-N methyl 5-(2-chlorophenyl)-5-cyano-2-oxocyclohexane-1-carboxylate Chemical compound C1CC(=O)C(C(=O)OC)CC1(C#N)C1=CC=CC=C1Cl GISBVGIZKAWADG-UHFFFAOYSA-N 0.000 description 2
CNDBGURZBCDQMK-UHFFFAOYSA-N methyl 5-cyano-2-oxo-5-thiophen-2-ylcyclohexane-1-carboxylate Chemical compound C1CC(=O)C(C(=O)OC)CC1(C#N)C1=CC=CS1 CNDBGURZBCDQMK-UHFFFAOYSA-N 0.000 description 2
DDXHXOUCNILGDS-UHFFFAOYSA-N methyl 5-cyano-5-(3,4-dimethoxyphenyl)-2-oxocyclohexane-1-carboxylate Chemical compound C1CC(=O)C(C(=O)OC)CC1(C#N)C1=CC=C(OC)C(OC)=C1 DDXHXOUCNILGDS-UHFFFAOYSA-N 0.000 description 2
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
229960002216 methylparaben Drugs 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
239000007935 oral tablet Substances 0.000 description 2
125000000962 organic group Chemical group 0.000 description 2
239000003182 parenteral nutrition solution Substances 0.000 description 2
239000008188 pellet Substances 0.000 description 2
XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 2
229940066842 petrolatum Drugs 0.000 description 2
235000019271 petrolatum Nutrition 0.000 description 2
CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 description 2
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
229940068968 polysorbate 80 Drugs 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical group CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 2
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 2
229940093625 propylene glycol monostearate Drugs 0.000 description 2
229960003415 propylparaben Drugs 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
239000003352 sequestering agent Substances 0.000 description 2
235000013874 shellac Nutrition 0.000 description 2
239000004208 shellac Substances 0.000 description 2
229940113147 shellac Drugs 0.000 description 2
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
229960001462 sodium cyclamate Drugs 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
235000011069 sorbitan monooleate Nutrition 0.000 description 2
239000001593 sorbitan monooleate Substances 0.000 description 2
229940035049 sorbitan monooleate Drugs 0.000 description 2
239000008117 stearic acid Substances 0.000 description 2
239000008174 sterile solution Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000007940 sugar coated tablet Substances 0.000 description 2
230000009885 systemic effect Effects 0.000 description 2
239000011975 tartaric acid Substances 0.000 description 2
235000002906 tartaric acid Nutrition 0.000 description 2
150000003512 tertiary amines Chemical group 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
125000003944 tolyl group Chemical group 0.000 description 2
URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
239000003039 volatile agent Substances 0.000 description 2
238000005303 weighing Methods 0.000 description 2
HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
SBCDMKDTWODACO-UHFFFAOYSA-N 1,4-dibromo-2-methylbutane Chemical compound BrCC(C)CCBr SBCDMKDTWODACO-UHFFFAOYSA-N 0.000 description 1
IAEOYUUPFYJXHN-UHFFFAOYSA-N 1,5-diiodopentane Chemical compound ICCCCCI IAEOYUUPFYJXHN-UHFFFAOYSA-N 0.000 description 1
SOLBSHQYTQZTDJ-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-4-oxocyclohexane-1-carboxylic acid Chemical compound C=1C=C(Cl)C=C(Cl)C=1C1(C(=O)O)CCC(=O)CC1 SOLBSHQYTQZTDJ-UHFFFAOYSA-N 0.000 description 1
CVDLCBGRWYUNAK-UHFFFAOYSA-N 1-(2-methylphenyl)-4-oxocyclohexane-1-carboxylic acid Chemical compound CC1=CC=CC=C1C1(C(O)=O)CCC(=O)CC1 CVDLCBGRWYUNAK-UHFFFAOYSA-N 0.000 description 1
DBDIMKGSZUQUSV-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-4-oxocyclohexane-1-carboxylic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1C1(C(=O)O)CCC(=O)CC1 DBDIMKGSZUQUSV-UHFFFAOYSA-N 0.000 description 1
LTNKWPQQEPDIFC-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-oxocyclohexane-1-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCC(=O)CC1 LTNKWPQQEPDIFC-UHFFFAOYSA-N 0.000 description 1
KAGXEOOWZOCGCW-UHFFFAOYSA-N 1-(dibutylamino)-4-oxocyclohexane-1-carbonitrile Chemical compound CCCCN(CCCC)C1(C#N)CCC(=O)CC1 KAGXEOOWZOCGCW-UHFFFAOYSA-N 0.000 description 1
NJRAGRZEBIZJDO-UHFFFAOYSA-N 1-(diethylamino)-4-oxocyclohexane-1-carbonitrile Chemical compound CCN(CC)C1(C#N)CCC(=O)CC1 NJRAGRZEBIZJDO-UHFFFAOYSA-N 0.000 description 1
UUNQAATZPUTWDK-UHFFFAOYSA-N 1-(diethylamino)-4-oxocyclohexane-1-carbonitrile;ethene Chemical group C=C.CCN(CC)C1(C#N)CCC(=O)CC1 UUNQAATZPUTWDK-UHFFFAOYSA-N 0.000 description 1
XCFYRDPDPPQNDL-UHFFFAOYSA-N 1-(dimethylamino)-4-oxocyclohexane-1-carbonitrile;ethene Chemical group C=C.CN(C)C1(C#N)CCC(=O)CC1 XCFYRDPDPPQNDL-UHFFFAOYSA-N 0.000 description 1
AZEBONMIPMABAN-UHFFFAOYSA-N 1-(dipropylamino)-4-oxocyclohexane-1-carbonitrile Chemical compound CCCN(CCC)C1(C#N)CCC(=O)CC1 AZEBONMIPMABAN-UHFFFAOYSA-N 0.000 description 1
DMCVQWWWVBBQRG-UHFFFAOYSA-N 1-[butyl(ethyl)amino]-4-oxocyclohexane-1-carbonitrile Chemical compound CCCCN(CC)C1(C#N)CCC(=O)CC1 DMCVQWWWVBBQRG-UHFFFAOYSA-N 0.000 description 1
JUMYXYKTCCJPIV-UHFFFAOYSA-N 1-[butyl(methyl)amino]-4-oxocyclohexane-1-carbonitrile;ethene Chemical group C=C.CCCCN(C)C1(C#N)CCC(=O)CC1 JUMYXYKTCCJPIV-UHFFFAOYSA-N 0.000 description 1
LHRMRNVMRQPGRP-UHFFFAOYSA-N 1-[cyclopropyl(methyl)amino]-4-oxocyclohexane-1-carbonitrile Chemical compound C1CC(=O)CCC1(C#N)N(C)C1CC1 LHRMRNVMRQPGRP-UHFFFAOYSA-N 0.000 description 1
FTCXWNUJMSGUKP-UHFFFAOYSA-N 1-amino-4-oxocyclohexane-1-carbonitrile Chemical compound N#CC1(N)CCC(=O)CC1 FTCXWNUJMSGUKP-UHFFFAOYSA-N 0.000 description 1
XLQSXGGDTHANLN-UHFFFAOYSA-N 1-bromo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Br)C=C1 XLQSXGGDTHANLN-UHFFFAOYSA-N 0.000 description 1
NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
QXQAPNSHUJORMC-UHFFFAOYSA-N 1-chloro-4-propylbenzene Chemical compound CCCC1=CC=C(Cl)C=C1 QXQAPNSHUJORMC-UHFFFAOYSA-N 0.000 description 1
BLXSFCHWMBESKV-UHFFFAOYSA-N 1-iodopentane Chemical compound CCCCCI BLXSFCHWMBESKV-UHFFFAOYSA-N 0.000 description 1
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical group CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
VJARIBGMDPJLCL-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)acetonitrile Chemical compound ClC1=CC=C(CC#N)C(Cl)=C1 VJARIBGMDPJLCL-UHFFFAOYSA-N 0.000 description 1
AOEJUUCUKRUCEF-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)acetonitrile Chemical compound ClC1=CC=CC(Cl)=C1CC#N AOEJUUCUKRUCEF-UHFFFAOYSA-N 0.000 description 1
VSSZEBGUCILFSV-UHFFFAOYSA-N 2-(2-bromo-5-methoxyphenyl)acetonitrile Chemical compound COC1=CC=C(Br)C(CC#N)=C1 VSSZEBGUCILFSV-UHFFFAOYSA-N 0.000 description 1
MRDUURPIPLIGQX-UHFFFAOYSA-N 2-(2-chlorophenyl)acetonitrile Chemical compound ClC1=CC=CC=C1CC#N MRDUURPIPLIGQX-UHFFFAOYSA-N 0.000 description 1
LLLAUEJCYCBLPM-UHFFFAOYSA-N 2-(2-ethylphenyl)acetonitrile Chemical compound CCC1=CC=CC=C1CC#N LLLAUEJCYCBLPM-UHFFFAOYSA-N 0.000 description 1
WGIMXKDCVCTHGW-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCOCCO WGIMXKDCVCTHGW-UHFFFAOYSA-N 0.000 description 1
QWZNCAFWRZZJMA-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)acetonitrile Chemical compound ClC1=CC=C(CC#N)C=C1Cl QWZNCAFWRZZJMA-UHFFFAOYSA-N 0.000 description 1
WIQQDLOECFMMPQ-UHFFFAOYSA-N 2-(3-bromo-5-propoxyphenyl)acetonitrile Chemical compound CCCOC1=CC(Br)=CC(CC#N)=C1 WIQQDLOECFMMPQ-UHFFFAOYSA-N 0.000 description 1
GAUHFGRZXPVMQD-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)acetonitrile Chemical compound FC1=CC=C(CC#N)C=C1Cl GAUHFGRZXPVMQD-UHFFFAOYSA-N 0.000 description 1
GTIKLPYCSAMPNG-UHFFFAOYSA-N 2-(3-chlorophenyl)acetonitrile Chemical compound ClC1=CC=CC(CC#N)=C1 GTIKLPYCSAMPNG-UHFFFAOYSA-N 0.000 description 1
WOJADIOTNFDWNQ-UHFFFAOYSA-N 2-(3-methylphenyl)acetonitrile Chemical group CC1=CC=CC(CC#N)=C1 WOJADIOTNFDWNQ-UHFFFAOYSA-N 0.000 description 1
MFHFWRBXPQDZSA-UHFFFAOYSA-N 2-(4-bromophenyl)acetonitrile Chemical compound BrC1=CC=C(CC#N)C=C1 MFHFWRBXPQDZSA-UHFFFAOYSA-N 0.000 description 1
JHQBLYITVCBGTO-UHFFFAOYSA-N 2-(4-fluorophenyl)acetonitrile Chemical compound FC1=CC=C(CC#N)C=C1 JHQBLYITVCBGTO-UHFFFAOYSA-N 0.000 description 1
KEQMCCXBUGKEPF-UHFFFAOYSA-N 2-(4-fluorophenyl)cyclohexan-1-one Chemical compound C1=CC(F)=CC=C1C1C(=O)CCCC1 KEQMCCXBUGKEPF-UHFFFAOYSA-N 0.000 description 1
PACGLQCRGWFBJH-UHFFFAOYSA-N 2-(4-methoxyphenyl)acetonitrile Chemical compound COC1=CC=C(CC#N)C=C1 PACGLQCRGWFBJH-UHFFFAOYSA-N 0.000 description 1
RNHKXHKUKJXLAU-UHFFFAOYSA-N 2-(4-methylphenyl)acetonitrile Chemical compound CC1=CC=C(CC#N)C=C1 RNHKXHKUKJXLAU-UHFFFAOYSA-N 0.000 description 1
DPZHKLJPVMYFCU-UHFFFAOYSA-N 2-(5-bromopyridin-2-yl)acetonitrile Chemical compound BrC1=CC=C(CC#N)N=C1 DPZHKLJPVMYFCU-UHFFFAOYSA-N 0.000 description 1
YVPGMOIUQBMWLU-UHFFFAOYSA-N 2-(5-chloro-2-methoxyphenyl)acetonitrile Chemical compound COC1=CC=C(Cl)C=C1CC#N YVPGMOIUQBMWLU-UHFFFAOYSA-N 0.000 description 1
LWXRVGSVNXASAD-UHFFFAOYSA-N 2-(methylamino)cyclohexan-1-one Chemical compound CNC1CCCCC1=O LWXRVGSVNXASAD-UHFFFAOYSA-N 0.000 description 1
CQACLTPFFDNBEY-UHFFFAOYSA-N 2-[3,5-di(propan-2-yl)phenyl]acetonitrile Chemical compound CC(C)C1=CC(CC#N)=CC(C(C)C)=C1 CQACLTPFFDNBEY-UHFFFAOYSA-N 0.000 description 1
SIUAYRSKLKTMSP-UHFFFAOYSA-N 2-amino-4-(2-methylphenyl)cyclohexan-1-one Chemical compound NC1C(CCC(C1)C1=C(C=CC=C1)C)=O SIUAYRSKLKTMSP-UHFFFAOYSA-N 0.000 description 1
AYOHZNGDXKKACQ-UHFFFAOYSA-N 2-amino-4-methyl-4-(2-methylphenyl)cyclohexan-1-one Chemical compound CC1(CC(C(CC1)=O)N)C1=C(C=CC=C1)C AYOHZNGDXKKACQ-UHFFFAOYSA-N 0.000 description 1
KMLPEYHLAKSCGX-UHFFFAOYSA-N 2-aminocyclohexan-1-one Chemical compound NC1CCCCC1=O KMLPEYHLAKSCGX-UHFFFAOYSA-N 0.000 description 1
BGVPOAOYLKPGPH-UHFFFAOYSA-N 2-butyl-4-(4-chlorophenyl)-4-(dimethylamino)cyclohexan-1-one Chemical compound C1CC(=O)C(CCCC)CC1(N(C)C)C1=CC=C(Cl)C=C1 BGVPOAOYLKPGPH-UHFFFAOYSA-N 0.000 description 1
NILLIUYSJFTTRH-UHFFFAOYSA-N 2-cyclopentylacetyl chloride Chemical group ClC(=O)CC1CCCC1 NILLIUYSJFTTRH-UHFFFAOYSA-N 0.000 description 1
GNXFOGHNGIVQEH-UHFFFAOYSA-N 2-hydroxy-3-(2-methoxyphenoxy)propyl carbamate Chemical compound COC1=CC=CC=C1OCC(O)COC(N)=O GNXFOGHNGIVQEH-UHFFFAOYSA-N 0.000 description 1
DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 description 1
VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
BPBDZXFJDMJLIB-UHFFFAOYSA-N 2-phenylpropane-1,3-diol Chemical compound OCC(CO)C1=CC=CC=C1 BPBDZXFJDMJLIB-UHFFFAOYSA-N 0.000 description 1
DBYUXTHCHXLVIU-UHFFFAOYSA-N 2-prop-2-enylpropane-1,3-diol Chemical compound OCC(CO)CC=C DBYUXTHCHXLVIU-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
CLSHQIDDCJTHAJ-UHFFFAOYSA-N 2-thienylacetonitrile Chemical compound N#CCC1=CC=CS1 CLSHQIDDCJTHAJ-UHFFFAOYSA-N 0.000 description 1
SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
XRVBOMBNAMKHMX-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-4-oxocyclohexane-1-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1C(=O)CCC(C#N)C1 XRVBOMBNAMKHMX-UHFFFAOYSA-N 0.000 description 1
HQLLUIGQAYVFBX-UHFFFAOYSA-N 3-(3-bromo-4-methoxyphenyl)propanenitrile Chemical compound COC1=CC=C(CCC#N)C=C1Br HQLLUIGQAYVFBX-UHFFFAOYSA-N 0.000 description 1
GJVHYHXGNIMMNO-UHFFFAOYSA-N 3-(3-methoxyphenyl)propanenitrile Chemical compound COC1=CC=CC(CCC#N)=C1 GJVHYHXGNIMMNO-UHFFFAOYSA-N 0.000 description 1
MHUBNPUIDRLFLF-UHFFFAOYSA-N 3-ethyl-1,5-diiodopentane Chemical compound ICCC(CC)CCI MHUBNPUIDRLFLF-UHFFFAOYSA-N 0.000 description 1
ZYJBOXRFXTVWFJ-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-4-(methylamino)cyclohexan-1-one Chemical compound C=1C=C(Cl)C=C(Cl)C=1C1(NC)CCC(=O)CC1 ZYJBOXRFXTVWFJ-UHFFFAOYSA-N 0.000 description 1
WYTYHUVZLZQOIO-UHFFFAOYSA-N 4-(2,6-dichlorophenyl)-4-(dimethylamino)cyclohexan-1-one Chemical compound ClC=1C=CC=C(Cl)C=1C1(N(C)C)CCC(=O)CC1 WYTYHUVZLZQOIO-UHFFFAOYSA-N 0.000 description 1
LBRKVTZJMRYCSW-UHFFFAOYSA-N 4-(2-bromo-5-methoxyphenyl)-4-cyanoheptanedioic acid Chemical compound COC1=CC=C(Br)C(C(CCC(O)=O)(CCC(O)=O)C#N)=C1 LBRKVTZJMRYCSW-UHFFFAOYSA-N 0.000 description 1
RORJUYMUBPMPJK-UHFFFAOYSA-N 4-(2-chlorophenyl)-4-cyanoheptanedioic acid Chemical compound OC(=O)CCC(CCC(O)=O)(C#N)C1=CC=CC=C1Cl RORJUYMUBPMPJK-UHFFFAOYSA-N 0.000 description 1
QTOUEMFKFZHNHD-UHFFFAOYSA-N 4-(3-bromo-5-propoxyphenyl)-4-(dimethylamino)cyclohexan-1-one Chemical compound CCCOC1=CC(Br)=CC(C2(CCC(=O)CC2)N(C)C)=C1 QTOUEMFKFZHNHD-UHFFFAOYSA-N 0.000 description 1
DFGYQFSFRUERCY-UHFFFAOYSA-N 4-(3-bromo-5-propoxyphenyl)-4-cyanoheptanedioic acid Chemical compound CCCOC1=CC(Br)=CC(C(CCC(O)=O)(CCC(O)=O)C#N)=C1 DFGYQFSFRUERCY-UHFFFAOYSA-N 0.000 description 1
KMKBYQBALHBSDY-UHFFFAOYSA-N 4-(3-chloro-4-fluorophenyl)-4-(dimethylamino)cyclohexan-1-one;ethene Chemical group C=C.C=1C=C(F)C(Cl)=CC=1C1(N(C)C)CCC(=O)CC1 KMKBYQBALHBSDY-UHFFFAOYSA-N 0.000 description 1
CVXZFASTEGPVLO-UHFFFAOYSA-N 4-(3-chloro-4-fluorophenyl)-4-cyanoheptanedioic acid Chemical compound OC(=O)CCC(CCC(O)=O)(C#N)C1=CC=C(F)C(Cl)=C1 CVXZFASTEGPVLO-UHFFFAOYSA-N 0.000 description 1
KYBFFLXCYYOEEN-UHFFFAOYSA-N 4-(3-chlorophenyl)-4-(methylamino)cyclohexan-1-one Chemical compound C=1C=CC(Cl)=CC=1C1(NC)CCC(=O)CC1 KYBFFLXCYYOEEN-UHFFFAOYSA-N 0.000 description 1
GURABVHTYBSQPP-UHFFFAOYSA-N 4-(3-chlorophenyl)-4-isocyanatocyclohexan-1-one Chemical compound ClC1=CC=CC(C2(CCC(=O)CC2)N=C=O)=C1 GURABVHTYBSQPP-UHFFFAOYSA-N 0.000 description 1
YPMFRHKVMCASLC-UHFFFAOYSA-N 4-(3-hydroxyphenyl)-4-(pentylamino)cyclohexan-1-one Chemical compound C=1C=CC(O)=CC=1C1(NCCCCC)CCC(=O)CC1 YPMFRHKVMCASLC-UHFFFAOYSA-N 0.000 description 1
CDTWFWXFOOXCNK-UHFFFAOYSA-N 4-(3-hydroxyphenyl)-4-[methyl(2-methylpropyl)amino]cyclohexan-1-one Chemical compound C=1C=CC(O)=CC=1C1(N(C)CC(C)C)CCC(=O)CC1 CDTWFWXFOOXCNK-UHFFFAOYSA-N 0.000 description 1
CRYPVYDKWHKVKB-UHFFFAOYSA-N 4-(4-bromophenyl)-4-(methylamino)cyclohexan-1-one Chemical compound C=1C=C(Br)C=CC=1C1(NC)CCC(=O)CC1 CRYPVYDKWHKVKB-UHFFFAOYSA-N 0.000 description 1
SLVROOVHZQJVTD-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-(dibutylamino)-2-methylcyclohexan-1-one Chemical compound C=1C=C(Cl)C=CC=1C1(N(CCCC)CCCC)CCC(=O)C(C)C1 SLVROOVHZQJVTD-UHFFFAOYSA-N 0.000 description 1
AIHINZZITTUJSQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-(dibutylamino)cyclohexan-1-one Chemical group C=1C=C(Cl)C=CC=1C1(N(CCCC)CCCC)CCC(=O)CC1 AIHINZZITTUJSQ-UHFFFAOYSA-N 0.000 description 1
UQZSLUYUNTWVLW-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-(diethylamino)-2-methylcyclohexan-1-one Chemical compound C=1C=C(Cl)C=CC=1C1(N(CC)CC)CCC(=O)C(C)C1 UQZSLUYUNTWVLW-UHFFFAOYSA-N 0.000 description 1
DXGDEPVVYCEUER-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-(diethylamino)cyclohexan-1-one Chemical group C=1C=C(Cl)C=CC=1C1(N(CC)CC)CCC(=O)CC1 DXGDEPVVYCEUER-UHFFFAOYSA-N 0.000 description 1
UKYQPPAVEOVIOU-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-(dimethylamino)-2-propylcyclohexan-1-one Chemical compound C1CC(=O)C(CCC)CC1(N(C)C)C1=CC=C(Cl)C=C1 UKYQPPAVEOVIOU-UHFFFAOYSA-N 0.000 description 1
SJPSDLCPPZAXFT-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-(dipropylamino)-2-methylcyclohexan-1-one Chemical compound C=1C=C(Cl)C=CC=1C1(N(CCC)CCC)CCC(=O)C(C)C1 SJPSDLCPPZAXFT-UHFFFAOYSA-N 0.000 description 1
HHHUSCMHFOXOON-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-(dipropylamino)cyclohexan-1-one Chemical group C=1C=C(Cl)C=CC=1C1(N(CCC)CCC)CCC(=O)CC1 HHHUSCMHFOXOON-UHFFFAOYSA-N 0.000 description 1
XZJQTWSUUHKPFW-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-(methylamino)cyclohexan-1-one;ethene Chemical group C=C.C=1C=C(Cl)C=CC=1C1(NC)CCC(=O)CC1 XZJQTWSUUHKPFW-UHFFFAOYSA-N 0.000 description 1
JLYMYZVUPBBWNI-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-[cyclopropyl(methyl)amino]-2-methylcyclohexan-1-one Chemical compound C1CC(=O)C(C)CC1(C=1C=CC(Cl)=CC=1)N(C)C1CC1 JLYMYZVUPBBWNI-UHFFFAOYSA-N 0.000 description 1
RSOKIVNUHXAJMA-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-[cyclopropyl(methyl)amino]cyclohexan-1-one Chemical group C1CC(=O)CCC1(C=1C=CC(Cl)=CC=1)N(C)C1CC1 RSOKIVNUHXAJMA-UHFFFAOYSA-N 0.000 description 1
PQPUNVBDTHUQDJ-UHFFFAOYSA-N 4-(4-tert-butylphenyl)-4-(dimethylamino)cyclohexan-1-one Chemical compound C=1C=C(C(C)(C)C)C=CC=1C1(N(C)C)CCC(=O)CC1 PQPUNVBDTHUQDJ-UHFFFAOYSA-N 0.000 description 1
HLJMJZRGJNXSPG-UHFFFAOYSA-N 4-(5-chloro-2-methoxyphenyl)-4-(dimethylamino)cyclohexan-1-one;ethene Chemical group C=C.COC1=CC=C(Cl)C=C1C1(N(C)C)CCC(=O)CC1 HLJMJZRGJNXSPG-UHFFFAOYSA-N 0.000 description 1
CYAYVCULYUOYLB-UHFFFAOYSA-N 4-(5-chloro-2-methoxyphenyl)-4-cyanoheptanedioic acid Chemical compound COC1=CC=C(Cl)C=C1C(CCC(O)=O)(CCC(O)=O)C#N CYAYVCULYUOYLB-UHFFFAOYSA-N 0.000 description 1
CNDKEIBGYPQFCI-UHFFFAOYSA-N 4-(dibutylamino)-4-(3-hydroxyphenyl)cyclohexan-1-one Chemical compound C=1C=CC(O)=CC=1C1(N(CCCC)CCCC)CCC(=O)CC1 CNDKEIBGYPQFCI-UHFFFAOYSA-N 0.000 description 1
DLOROZLDLQVBAS-UHFFFAOYSA-N 4-(diethylamino)-4-(3-hydroxyphenyl)cyclohexan-1-one Chemical compound C=1C=CC(O)=CC=1C1(N(CC)CC)CCC(=O)CC1 DLOROZLDLQVBAS-UHFFFAOYSA-N 0.000 description 1
DHIOYTNYKKECLM-UHFFFAOYSA-N 4-(diethylamino)-4-(4-hydroxyphenyl)cyclohexan-1-one Chemical compound C=1C=C(O)C=CC=1C1(N(CC)CC)CCC(=O)CC1 DHIOYTNYKKECLM-UHFFFAOYSA-N 0.000 description 1
POYSOJOBADNWEB-UHFFFAOYSA-N 4-(diethylamino)-4-phenylcyclohexan-1-one;ethene Chemical group C=C.C=1C=CC=CC=1C1(N(CC)CC)CCC(=O)CC1 POYSOJOBADNWEB-UHFFFAOYSA-N 0.000 description 1
OXOCXAAVSPYGIT-UHFFFAOYSA-N 4-(diethylamino)-4-phenylcyclohexan-1-one;hydrochloride Chemical group Cl.C=1C=CC=CC=1C1(N(CC)CC)CCC(=O)CC1 OXOCXAAVSPYGIT-UHFFFAOYSA-N 0.000 description 1
CWJHNHRYODYWTQ-UHFFFAOYSA-N 4-(dimethylamino)-4-(2-ethylphenyl)cyclohexan-1-one Chemical compound CCC1=CC=CC=C1C1(N(C)C)CCC(=O)CC1 CWJHNHRYODYWTQ-UHFFFAOYSA-N 0.000 description 1
UVFQJZPHSHCIRD-UHFFFAOYSA-N 4-(dimethylamino)-4-(2-methylphenyl)cyclohexan-1-one;ethene Chemical group C=C.C=1C=CC=C(C)C=1C1(N(C)C)CCC(=O)CC1 UVFQJZPHSHCIRD-UHFFFAOYSA-N 0.000 description 1
SEZVYYDEZYVROQ-UHFFFAOYSA-N 4-(dimethylamino)-4-(2-methylphenyl)cyclohexan-1-one;hydroiodide Chemical compound I.C=1C=CC=C(C)C=1C1(N(C)C)CCC(=O)CC1 SEZVYYDEZYVROQ-UHFFFAOYSA-N 0.000 description 1
RSELKWGQXDWCSX-UHFFFAOYSA-N 4-(dimethylamino)-4-(3-hydroxyphenyl)-2-methylcyclohexan-1-one Chemical compound C1CC(=O)C(C)CC1(N(C)C)C1=CC=CC(O)=C1 RSELKWGQXDWCSX-UHFFFAOYSA-N 0.000 description 1
IUPGHGMWEUWJFD-UHFFFAOYSA-N 4-(dimethylamino)-4-[3,5-di(propan-2-yl)phenyl]cyclohexan-1-one Chemical compound CC(C)C1=CC(C(C)C)=CC(C2(CCC(=O)CC2)N(C)C)=C1 IUPGHGMWEUWJFD-UHFFFAOYSA-N 0.000 description 1
JVTPPPWXJXLVTG-UHFFFAOYSA-N 4-(dimethylamino)-4-[3-(trifluoromethyl)phenyl]cyclohexan-1-one;ethene Chemical group C=C.C=1C=CC(C(F)(F)F)=CC=1C1(N(C)C)CCC(=O)CC1 JVTPPPWXJXLVTG-UHFFFAOYSA-N 0.000 description 1
GKAZOZKLZBPWNM-UHFFFAOYSA-N 4-(dimethylamino)-4-naphthalen-1-ylcyclohexan-1-one Chemical compound C=1C=CC2=CC=CC=C2C=1C1(N(C)C)CCC(=O)CC1 GKAZOZKLZBPWNM-UHFFFAOYSA-N 0.000 description 1
RIZJRCWMWRGDSN-UHFFFAOYSA-N 4-(dimethylamino)-4-naphthalen-1-ylcyclohexan-1-one;ethene Chemical group C=C.C=1C=CC2=CC=CC=C2C=1C1(N(C)C)CCC(=O)CC1 RIZJRCWMWRGDSN-UHFFFAOYSA-N 0.000 description 1
QOOQUEXSTCOEDQ-UHFFFAOYSA-N 4-(dimethylamino)cyclohexan-1-one;ethene Chemical group C=C.CN(C)C1CCC(=O)CC1 QOOQUEXSTCOEDQ-UHFFFAOYSA-N 0.000 description 1
RTQFOMRZVJNCGS-UHFFFAOYSA-N 4-(dipropylamino)-4-(3-hydroxyphenyl)cyclohexan-1-one Chemical compound C=1C=CC(O)=CC=1C1(N(CCC)CCC)CCC(=O)CC1 RTQFOMRZVJNCGS-UHFFFAOYSA-N 0.000 description 1
VFIXXHWEDDZUDW-UHFFFAOYSA-N 4-[(3,3-dimethyl-2-oxobutyl)amino]-4-(3-phenylmethoxyphenyl)cyclohexan-1-one;ethene Chemical group C=C.C=1C=CC(OCC=2C=CC=CC=2)=CC=1C1(NCC(=O)C(C)(C)C)CCC(=O)CC1 VFIXXHWEDDZUDW-UHFFFAOYSA-N 0.000 description 1
ZCSUUUVYRMHTET-UHFFFAOYSA-N 4-[(3-bromo-4-methoxyphenyl)methyl]-4-(dimethylamino)cyclohexan-1-one Chemical compound C1=C(Br)C(OC)=CC=C1CC1(N(C)C)CCC(=O)CC1 ZCSUUUVYRMHTET-UHFFFAOYSA-N 0.000 description 1
KVSDQINCSAOVKD-UHFFFAOYSA-N 4-[(3-bromo-4-methoxyphenyl)methyl]-4-cyanoheptanedioic acid Chemical compound COC1=CC=C(CC(CCC(O)=O)(CCC(O)=O)C#N)C=C1Br KVSDQINCSAOVKD-UHFFFAOYSA-N 0.000 description 1
RUTJXCANLTUJDG-UHFFFAOYSA-N 4-[(3-methoxyphenyl)methyl]-4-pyrrolidin-1-ylcyclohexan-1-one Chemical compound COC1=CC=CC(CC2(CCC(=O)CC2)N2CCCC2)=C1 RUTJXCANLTUJDG-UHFFFAOYSA-N 0.000 description 1
MRVTUBHKQQFMBI-UHFFFAOYSA-N 4-[butyl(methyl)amino]-4-(3-phenylmethoxyphenyl)cyclohexan-1-one Chemical compound C=1C=CC(OCC=2C=CC=CC=2)=CC=1C1(N(C)CCCC)CCC(=O)CC1 MRVTUBHKQQFMBI-UHFFFAOYSA-N 0.000 description 1
WXNRWBPCAJACME-UHFFFAOYSA-N 4-[cyclohexylmethyl(methyl)amino]-4-(3-hydroxyphenyl)cyclohexan-1-one Chemical compound C1CC(=O)CCC1(C=1C=C(O)C=CC=1)N(C)CC1CCCCC1 WXNRWBPCAJACME-UHFFFAOYSA-N 0.000 description 1
JTIKXNOSCMXNAU-UHFFFAOYSA-N 4-[cyclohexylmethyl(methyl)amino]-4-(3-hydroxyphenyl)cyclohexan-1-one;ethene Chemical group C=C.C1CC(=O)CCC1(C=1C=C(O)C=CC=1)N(C)CC1CCCCC1 JTIKXNOSCMXNAU-UHFFFAOYSA-N 0.000 description 1
MCOYYBXGGGYCJL-UHFFFAOYSA-N 4-[cyclohexylmethyl(methyl)amino]-4-(3-phenylmethoxyphenyl)cyclohexan-1-one;ethene Chemical group C=C.C1CC(=O)CCC1(C=1C=C(OCC=2C=CC=CC=2)C=CC=1)N(C)CC1CCCCC1 MCOYYBXGGGYCJL-UHFFFAOYSA-N 0.000 description 1
ALTAMDVNRBPDGE-UHFFFAOYSA-N 4-[cyclopentylmethyl(methyl)amino]-4-(3-hydroxyphenyl)cyclohexan-1-one;ethene Chemical group C=C.C1CC(=O)CCC1(C=1C=C(O)C=CC=1)N(C)CC1CCCC1 ALTAMDVNRBPDGE-UHFFFAOYSA-N 0.000 description 1
GRJZEUYDOYCOOI-UHFFFAOYSA-N 4-[cyclopentylmethyl(methyl)amino]-4-(3-phenylmethoxyphenyl)cyclohexan-1-one;ethene Chemical group C=C.C1CC(=O)CCC1(C=1C=C(OCC=2C=CC=CC=2)C=CC=1)N(C)CC1CCCC1 GRJZEUYDOYCOOI-UHFFFAOYSA-N 0.000 description 1
OWIFPQKJOTXCLG-UHFFFAOYSA-N 4-[cyclopropylmethyl(methyl)amino]-4-(3-hydroxyphenyl)cyclohexan-1-one;ethene Chemical group C=C.C1CC(=O)CCC1(C=1C=C(O)C=CC=1)N(C)CC1CC1 OWIFPQKJOTXCLG-UHFFFAOYSA-N 0.000 description 1
JWHDSCYHIAFJJW-UHFFFAOYSA-N 4-[ethyl(methyl)amino]-4-(3-hydroxyphenyl)cyclohexan-1-one Chemical compound C=1C=CC(O)=CC=1C1(N(C)CC)CCC(=O)CC1 JWHDSCYHIAFJJW-UHFFFAOYSA-N 0.000 description 1
XPYQFIISZQCINN-QVXDJYSKSA-N 4-amino-1-[(2r,3e,4s,5r)-3-(fluoromethylidene)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrate Chemical compound O.O=C1N=C(N)C=CN1[C@H]1C(=C/F)/[C@H](O)[C@@H](CO)O1 XPYQFIISZQCINN-QVXDJYSKSA-N 0.000 description 1
WPIAALQAEQXXIG-UHFFFAOYSA-N 4-amino-4-(3-methoxyphenyl)cyclohexan-1-one Chemical compound COC1=CC=CC(C2(N)CCC(=O)CC2)=C1 WPIAALQAEQXXIG-UHFFFAOYSA-N 0.000 description 1
MNFRVKFDPQELFV-UHFFFAOYSA-N 4-amino-4-(3-methoxyphenyl)cyclohexan-1-one;ethene Chemical group C=C.COC1=CC=CC(C2(N)CCC(=O)CC2)=C1 MNFRVKFDPQELFV-UHFFFAOYSA-N 0.000 description 1
GGQWGPJQKSYAFM-UHFFFAOYSA-N 4-amino-4-[(3-methoxyphenyl)methyl]cyclohexan-1-one Chemical compound COC1=CC=CC(CC2(N)CCC(=O)CC2)=C1 GGQWGPJQKSYAFM-UHFFFAOYSA-N 0.000 description 1
OTCYOBLTAQTFPW-UHFFFAOYSA-N 4-aminocyclohexan-1-one Chemical compound NC1CCC(=O)CC1 OTCYOBLTAQTFPW-UHFFFAOYSA-N 0.000 description 1
GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
CSPMXJGAUSRZHA-UHFFFAOYSA-N 4-cyano-4-(2-ethylphenyl)heptanedioic acid Chemical compound CCC1=CC=CC=C1C(CCC(O)=O)(CCC(O)=O)C#N CSPMXJGAUSRZHA-UHFFFAOYSA-N 0.000 description 1
WFDHPIYTZIXJEU-UHFFFAOYSA-N 4-cyano-4-[3,5-di(propan-2-yl)phenyl]heptanedioic acid Chemical compound CC(C)C1=CC(C(C)C)=CC(C(CCC(O)=O)(CCC(O)=O)C#N)=C1 WFDHPIYTZIXJEU-UHFFFAOYSA-N 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
ALEVUYMOJKJJSA-UHFFFAOYSA-N 4-hydroxy-2-propylbenzoic acid Chemical class CCCC1=CC(O)=CC=C1C(O)=O ALEVUYMOJKJJSA-UHFFFAOYSA-N 0.000 description 1
BXBJZYXQHHPVGO-UHFFFAOYSA-N 4-hydroxycyclohexan-1-one Chemical compound OC1CCC(=O)CC1 BXBJZYXQHHPVGO-UHFFFAOYSA-N 0.000 description 1
BJMXOOGSNSYCNN-UHFFFAOYSA-N 4-isocyanatocyclohexan-1-one Chemical compound O=C=NC1CCC(=O)CC1 BJMXOOGSNSYCNN-UHFFFAOYSA-N 0.000 description 1
QIWQJGMBIABGRX-UHFFFAOYSA-N 4-oxocyclohexane-1-carbonitrile Chemical compound O=C1CCC(C#N)CC1 QIWQJGMBIABGRX-UHFFFAOYSA-N 0.000 description 1
YKAYMASDSHFOGI-UHFFFAOYSA-N 4-phenylcyclohexan-1-one Chemical compound C1CC(=O)CCC1C1=CC=CC=C1 YKAYMASDSHFOGI-UHFFFAOYSA-N 0.000 description 1
ZNDMWZIAZJLETD-UHFFFAOYSA-N 4-piperidin-1-ylcyclohexan-1-one Chemical compound C1CC(=O)CCC1N1CCCCC1 ZNDMWZIAZJLETD-UHFFFAOYSA-N 0.000 description 1
RDGIABKZGSKWCC-UHFFFAOYSA-N 4-pyrrolidin-1-ylcyclohexan-1-one Chemical compound C1CC(=O)CCC1N1CCCC1 RDGIABKZGSKWCC-UHFFFAOYSA-N 0.000 description 1
PJJGZPJJTHBVMX-UHFFFAOYSA-N 5,7-Dihydroxyisoflavone Chemical compound C=1C(O)=CC(O)=C(C2=O)C=1OC=C2C1=CC=CC=C1 PJJGZPJJTHBVMX-UHFFFAOYSA-N 0.000 description 1
RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 1
USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 description 1
NSECBSWZJRNOPE-UHFFFAOYSA-N 8-isocyanato-8-thiophen-2-yl-1,4-dioxaspiro[4.5]decane Chemical compound C1CC(N=C=O)(C=2SC=CC=2)CCC21OCCO2 NSECBSWZJRNOPE-UHFFFAOYSA-N 0.000 description 1
FVXOGNXUZZJKFT-UHFFFAOYSA-N 8-phenyl-1,4-dioxaspiro[4.5]decan-8-amine;hydrochloride Chemical compound Cl.C1CC(N)(C=2C=CC=CC=2)CCC21OCCO2 FVXOGNXUZZJKFT-UHFFFAOYSA-N 0.000 description 1
ZYSLMLVZXZLRMH-UHFFFAOYSA-N 8-thiophen-2-yl-1,4-dioxaspiro[4.5]decane-8-carbonitrile Chemical compound C1CC(C#N)(C=2SC=CC=2)CCC21OCCO2 ZYSLMLVZXZLRMH-UHFFFAOYSA-N 0.000 description 1
IWMOIUMNZYJEDO-UHFFFAOYSA-N 8-thiophen-2-yl-1,4-dioxaspiro[4.5]decane-8-carboxylic acid Chemical compound C1CC(C(=O)O)(C=2SC=CC=2)CCC21OCCO2 IWMOIUMNZYJEDO-UHFFFAOYSA-N 0.000 description 1
206010049589 Afterbirth pain Diseases 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
208000008035 Back Pain Diseases 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
229910014265 BrCl Inorganic materials 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
206010006803 Burns third degree Diseases 0.000 description 1
206010006811 Bursitis Diseases 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
CRSYSYYRSDARMI-UHFFFAOYSA-N C=C.CNC1C(CCCC1)=O Chemical group C=C.CNC1C(CCCC1)=O CRSYSYYRSDARMI-UHFFFAOYSA-N 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
101100453921 Caenorhabditis elegans kin-29 gene Proteins 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
238000006969 Curtius rearrangement reaction Methods 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
206010012335 Dependence Diseases 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
208000005171 Dysmenorrhea Diseases 0.000 description 1
206010013935 Dysmenorrhoea Diseases 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
241000283086 Equidae Species 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
238000003747 Grignard reaction Methods 0.000 description 1
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
PWWVAXIEGOYWEE-UHFFFAOYSA-N Isophenergan Chemical compound C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 PWWVAXIEGOYWEE-UHFFFAOYSA-N 0.000 description 1
241000218194 Laurales Species 0.000 description 1
208000008930 Low Back Pain Diseases 0.000 description 1
241000195947 Lycopodium Species 0.000 description 1
NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
DUGOZIWVEXMGBE-UHFFFAOYSA-N Methylphenidate Chemical compound C=1C=CC=CC=1C(C(=O)OC)C1CCCCN1 DUGOZIWVEXMGBE-UHFFFAOYSA-N 0.000 description 1
FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 description 1
229920000715 Mucilage Polymers 0.000 description 1
208000007101 Muscle Cramp Diseases 0.000 description 1
HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
AHZDNENJBHSIPO-UHFFFAOYSA-N N-(5-methyl-2-oxo-5-phenylcyclohexyl)acetamide Chemical compound CC1(CC(C(CC1)=O)NC(C)=O)C1=CC=CC=C1 AHZDNENJBHSIPO-UHFFFAOYSA-N 0.000 description 1
208000018526 Narcotic-Related disease Diseases 0.000 description 1
BRUQQQPBMZOVGD-XFKAJCMBSA-N Oxycodone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C BRUQQQPBMZOVGD-XFKAJCMBSA-N 0.000 description 1
UQCNKQCJZOAFTQ-ISWURRPUSA-N Oxymorphone Chemical compound O([C@H]1C(CC[C@]23O)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O UQCNKQCJZOAFTQ-ISWURRPUSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
235000021314 Palmitic acid Nutrition 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
208000004550 Postoperative Pain Diseases 0.000 description 1
HCBIBCJNVBAKAB-UHFFFAOYSA-N Procaine hydrochloride Chemical compound Cl.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 HCBIBCJNVBAKAB-UHFFFAOYSA-N 0.000 description 1
208000004756 Respiratory Insufficiency Diseases 0.000 description 1
206010038678 Respiratory depression Diseases 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
208000005392 Spasm Diseases 0.000 description 1
208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 1
240000006474 Theobroma bicolor Species 0.000 description 1
208000003443 Unconsciousness Diseases 0.000 description 1
235000007244 Zea mays Nutrition 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
CJPIXXHXIWNSRI-UHFFFAOYSA-N [3-[1-(cyclopropylmethylamino)-4-oxocyclohexyl]phenyl] acetate Chemical compound CC(=O)OC1=CC=CC(C2(CCC(=O)CC2)NCC2CC2)=C1 CJPIXXHXIWNSRI-UHFFFAOYSA-N 0.000 description 1
NUCVELKHTZCJRK-UHFFFAOYSA-N [3-[1-(dimethylamino)-4-oxocyclohexyl]phenyl] propanoate Chemical compound CCC(=O)OC1=CC=CC(C2(CCC(=O)CC2)N(C)C)=C1 NUCVELKHTZCJRK-UHFFFAOYSA-N 0.000 description 1
AIJAUECXHXLJFP-UHFFFAOYSA-N [3-[1-[butyl(methyl)amino]-4-oxocyclohexyl]phenyl] acetate;hydrochloride Chemical compound Cl.C=1C=CC(OC(C)=O)=CC=1C1(N(C)CCCC)CCC(=O)CC1 AIJAUECXHXLJFP-UHFFFAOYSA-N 0.000 description 1
PEJYMAAPDUOCFO-UHFFFAOYSA-N [3-[1-[butyl(methyl)amino]-4-oxocyclohexyl]phenyl] propanoate Chemical compound C=1C=CC(OC(=O)CC)=CC=1C1(N(C)CCCC)CCC(=O)CC1 PEJYMAAPDUOCFO-UHFFFAOYSA-N 0.000 description 1
HARCQCNNQKKCNW-UHFFFAOYSA-N [3-[1-[methyl(propyl)amino]-4-oxocyclohexyl]phenyl] acetate Chemical compound C=1C=CC(OC(C)=O)=CC=1C1(N(C)CCC)CCC(=O)CC1 HARCQCNNQKKCNW-UHFFFAOYSA-N 0.000 description 1
LKLXYOTVNSZDDE-UHFFFAOYSA-N [C].O=C1CCCCC1 Chemical group [C].O=C1CCCCC1 LKLXYOTVNSZDDE-UHFFFAOYSA-N 0.000 description 1
JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
GAMPNQJDUFQVQO-UHFFFAOYSA-N acetic acid;phthalic acid Chemical class CC(O)=O.OC(=O)C1=CC=CC=C1C(O)=O GAMPNQJDUFQVQO-UHFFFAOYSA-N 0.000 description 1
229940081735 acetylcellulose Drugs 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
230000002730 additional effect Effects 0.000 description 1
208000009956 adenocarcinoma Diseases 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
239000008272 agar Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
230000004075 alteration Effects 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
238000002266 amputation Methods 0.000 description 1
239000002269 analeptic agent Substances 0.000 description 1
230000003555 analeptic effect Effects 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
230000001387 anti-histamine Effects 0.000 description 1
229940125715 antihistaminic agent Drugs 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
230000002917 arthritic effect Effects 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
230000003385 bacteriostatic effect Effects 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
239000012179 bayberry wax Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
229960000686 benzalkonium chloride Drugs 0.000 description 1
UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 1
229960001950 benzethonium chloride Drugs 0.000 description 1
229960004365 benzoic acid Drugs 0.000 description 1
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
150000005524 benzylchlorides Chemical class 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
230000036760 body temperature Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
QARVLSVVCXYDNA-IDEBNGHGSA-N bromobenzene Chemical group Br[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 QARVLSVVCXYDNA-IDEBNGHGSA-N 0.000 description 1
235000014121 butter Nutrition 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
229960001948 caffeine Drugs 0.000 description 1
VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
229940043202 calcium cyclamate Drugs 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
125000005587 carbonate group Chemical group 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
229940105329 carboxymethylcellulose Drugs 0.000 description 1
OFZCIYFFPZCNJE-UHFFFAOYSA-N carisoprodol Chemical compound NC(=O)OCC(C)(CCC)COC(=O)NC(C)C OFZCIYFFPZCNJE-UHFFFAOYSA-N 0.000 description 1
229960004587 carisoprodol Drugs 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
229940081734 cellulose acetate phthalate Drugs 0.000 description 1
229960000541 cetyl alcohol Drugs 0.000 description 1
150000005829 chemical entities Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
229960004782 chlordiazepoxide Drugs 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
SOYKEARSMXGVTM-UHFFFAOYSA-N chlorphenamine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 SOYKEARSMXGVTM-UHFFFAOYSA-N 0.000 description 1
229960003291 chlorphenamine Drugs 0.000 description 1
TZFWDZFKRBELIQ-UHFFFAOYSA-N chlorzoxazone Chemical compound ClC1=CC=C2OC(O)=NC2=C1 TZFWDZFKRBELIQ-UHFFFAOYSA-N 0.000 description 1
229960003633 chlorzoxazone Drugs 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
229940117975 chromium trioxide Drugs 0.000 description 1
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
238000004040 coloring Methods 0.000 description 1
230000002301 combined effect Effects 0.000 description 1
230000001609 comparable effect Effects 0.000 description 1
238000013329 compounding Methods 0.000 description 1
238000007906 compression Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
230000000332 continued effect Effects 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
230000001054 cortical effect Effects 0.000 description 1
239000003246 corticosteroid Substances 0.000 description 1
229960001334 corticosteroids Drugs 0.000 description 1
150000001896 cresols Chemical class 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000000000 cycloalkoxy group Chemical group 0.000 description 1
RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical group ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
150000001934 cyclohexanes Chemical class 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
WEPUZBYKXNKSDH-UHFFFAOYSA-N cyclopentanecarbonyl chloride Chemical group ClC(=O)C1CCCC1 WEPUZBYKXNKSDH-UHFFFAOYSA-N 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
229960001140 cyproheptadine Drugs 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
229960003957 dexamethasone Drugs 0.000 description 1
UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 description 1
229960004193 dextropropoxyphene Drugs 0.000 description 1
239000008355 dextrose injection Substances 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
238000007865 diluting Methods 0.000 description 1
YYDPXKCGTLUMLO-UHFFFAOYSA-N dimethyl 4-(2-chlorophenyl)-4-cyanoheptanedioate Chemical compound COC(=O)CCC(CCC(=O)OC)(C#N)C1=CC=CC=C1Cl YYDPXKCGTLUMLO-UHFFFAOYSA-N 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical group CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000002662 enteric coated tablet Substances 0.000 description 1
BOZDRSCMRACYBT-UHFFFAOYSA-N ethene;4-(3-hydroxyphenyl)-4-[methyl(propyl)amino]cyclohexan-1-one Chemical group C=C.C=1C=CC(O)=CC=1C1(N(C)CCC)CCC(=O)CC1 BOZDRSCMRACYBT-UHFFFAOYSA-N 0.000 description 1
BTHRCEZAVBGRAL-UHFFFAOYSA-N ethene;4-(3-methoxyphenyl)-4-pyrrolidin-1-ylcyclohexan-1-one Chemical group C=C.COC1=CC=CC(C2(CCC(=O)CC2)N2CCCC2)=C1 BTHRCEZAVBGRAL-UHFFFAOYSA-N 0.000 description 1
XKBZLLWPZPXSAA-UHFFFAOYSA-N ethene;4-(methylamino)-4-(3-phenylmethoxyphenyl)cyclohexan-1-one Chemical group C=C.C=1C=CC(OCC=2C=CC=CC=2)=CC=1C1(NC)CCC(=O)CC1 XKBZLLWPZPXSAA-UHFFFAOYSA-N 0.000 description 1
UQMFLGHSRUOOIH-UHFFFAOYSA-N ethene;4-(methylamino)-4-phenylcyclohexan-1-one Chemical group C=C.C=1C=CC=CC=1C1(NC)CCC(=O)CC1 UQMFLGHSRUOOIH-UHFFFAOYSA-N 0.000 description 1
JWZYCTWQBSNVFS-UHFFFAOYSA-N ethene;4-[(3-methoxyphenyl)methyl]-4-(methylamino)cyclohexan-1-one Chemical group C=C.C=1C=CC(OC)=CC=1CC1(NC)CCC(=O)CC1 JWZYCTWQBSNVFS-UHFFFAOYSA-N 0.000 description 1
GXDLAQKVZFVTOT-UHFFFAOYSA-N ethene;4-[(3-methoxyphenyl)methyl]-4-pyrrolidin-1-ylcyclohexan-1-one Chemical group C=C.COC1=CC=CC(CC2(CCC(=O)CC2)N2CCCC2)=C1 GXDLAQKVZFVTOT-UHFFFAOYSA-N 0.000 description 1
JURPNDYBNFGDTM-UHFFFAOYSA-N ethene;4-[2-hydroxyethyl(methyl)amino]-4-phenylcyclohexan-1-one Chemical group C=C.C=1C=CC=CC=1C1(N(CCO)C)CCC(=O)CC1 JURPNDYBNFGDTM-UHFFFAOYSA-N 0.000 description 1
OIEPQEATFLUYFO-UHFFFAOYSA-N ethene;4-[ethyl(methyl)amino]-4-(3-hydroxyphenyl)cyclohexan-1-one Chemical group C=C.C=1C=CC(O)=CC=1C1(N(C)CC)CCC(=O)CC1 OIEPQEATFLUYFO-UHFFFAOYSA-N 0.000 description 1
HOAOLRSSVAUPKT-UHFFFAOYSA-N ethene;4-isocyanato-4-(2-methylphenyl)cyclohexan-1-one Chemical group C=C.CC1=CC=CC=C1C1(N=C=O)CCC(=O)CC1 HOAOLRSSVAUPKT-UHFFFAOYSA-N 0.000 description 1
NHGORTNXAIJADY-UHFFFAOYSA-N ethene;4-isocyanato-4-[(3-methoxyphenyl)methyl]cyclohexan-1-one Chemical group C=C.COC1=CC=CC(CC2(CCC(=O)CC2)N=C=O)=C1 NHGORTNXAIJADY-UHFFFAOYSA-N 0.000 description 1
OSKJQOMDJWDUEQ-UHFFFAOYSA-N ethene;4-isocyanato-4-phenylcyclohexan-1-one Chemical group C=C.C=1C=CC=CC=1C1(N=C=O)CCC(=O)CC1 OSKJQOMDJWDUEQ-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
LFVPBERIVUNMGV-UHFFFAOYSA-N fasudil hydrochloride Chemical compound Cl.C=1C=CC2=CN=CC=C2C=1S(=O)(=O)N1CCCNCC1 LFVPBERIVUNMGV-UHFFFAOYSA-N 0.000 description 1
239000007941 film coated tablet Substances 0.000 description 1
239000007888 film coating Substances 0.000 description 1
238000009501 film coating Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011888 foil Substances 0.000 description 1
230000037406 food intake Effects 0.000 description 1
230000001408 fungistatic effect Effects 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000008103 glucose Substances 0.000 description 1
229960005150 glycerol Drugs 0.000 description 1
229940075507 glyceryl monostearate Drugs 0.000 description 1
229940074050 glyceryl myristate Drugs 0.000 description 1
239000001087 glyceryl triacetate Substances 0.000 description 1
235000013773 glyceryl triacetate Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
229910000043 hydrogen iodide Inorganic materials 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
WVLOADHCBXTIJK-YNHQPCIGSA-N hydromorphone Chemical compound O([C@H]1C(CC[C@H]23)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O WVLOADHCBXTIJK-YNHQPCIGSA-N 0.000 description 1
229960001410 hydromorphone Drugs 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
125000004464 hydroxyphenyl group Chemical group 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
239000007946 hypodermic tablet Substances 0.000 description 1
229960001680 ibuprofen Drugs 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
238000001802 infusion Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007951 isotonicity adjuster Substances 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
238000005907 ketalization reaction Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
229960004393 lidocaine hydrochloride Drugs 0.000 description 1
YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
229960003464 mefenamic acid Drugs 0.000 description 1
229960004815 meprobamate Drugs 0.000 description 1
YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 1
229960000582 mepyramine Drugs 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
229960001797 methadone Drugs 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
229940057952 methanol Drugs 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
229960002330 methocarbamol Drugs 0.000 description 1
ZNDKVDUPJGCVDA-UHFFFAOYSA-N methyl 5-(3-chlorophenyl)-5-cyano-2-oxocyclohexane-1-carboxylate Chemical compound C1CC(=O)C(C(=O)OC)CC1(C#N)C1=CC=CC(Cl)=C1 ZNDKVDUPJGCVDA-UHFFFAOYSA-N 0.000 description 1
BSPUHUQOTHCKHY-UHFFFAOYSA-N methyl 5-cyano-5-(2,4-dichlorophenyl)-2-oxocyclohexane-1-carboxylate Chemical compound C1CC(=O)C(C(=O)OC)CC1(C#N)C1=CC=C(Cl)C=C1Cl BSPUHUQOTHCKHY-UHFFFAOYSA-N 0.000 description 1
MMBYSSNHJFUDAN-UHFFFAOYSA-N methyl 5-cyano-5-(4-methoxyphenyl)-2-oxocyclohexane-1-carboxylate Chemical compound C1CC(=O)C(C(=O)OC)CC1(C#N)C1=CC=C(OC)C=C1 MMBYSSNHJFUDAN-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
229960001344 methylphenidate Drugs 0.000 description 1
229960004584 methylprednisolone Drugs 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
238000000465 moulding Methods 0.000 description 1
229940035363 muscle relaxants Drugs 0.000 description 1
239000003158 myorelaxant agent Substances 0.000 description 1
HCMTUKKLOVUFSF-UHFFFAOYSA-N n,n-dimethyl-8-thiophen-2-yl-1,4-dioxaspiro[4.5]decan-8-amine Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCC21OCCO2 HCMTUKKLOVUFSF-UHFFFAOYSA-N 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
VOVZXURTCKPRDQ-CQSZACIVSA-N n-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-5-(1h-pyrazol-5-yl)pyridine-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=NC=C(C(=O)NC=2C=CC(OC(F)(F)Cl)=CC=2)C=C1C1=CC=NN1 VOVZXURTCKPRDQ-CQSZACIVSA-N 0.000 description 1
125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
QHCCDDQKNUYGNC-UHFFFAOYSA-N n-ethylbutan-1-amine Chemical compound CCCCNCC QHCCDDQKNUYGNC-UHFFFAOYSA-N 0.000 description 1
VEBLEROFGPOMPB-UHFFFAOYSA-N n-methylcyclopropanamine Chemical compound CNC1CC1 VEBLEROFGPOMPB-UHFFFAOYSA-N 0.000 description 1
IOXXVNYDGIXMIP-UHFFFAOYSA-N n-methylprop-2-en-1-amine Chemical compound CNCC=C IOXXVNYDGIXMIP-UHFFFAOYSA-N 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical group OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
210000005036 nerve Anatomy 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical compound [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
239000000346 nonvolatile oil Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
QVYRGXJJSLMXQH-UHFFFAOYSA-N orphenadrine Chemical compound C=1C=CC=C(C)C=1C(OCCN(C)C)C1=CC=CC=C1 QVYRGXJJSLMXQH-UHFFFAOYSA-N 0.000 description 1
229960003941 orphenadrine Drugs 0.000 description 1
229960002085 oxycodone Drugs 0.000 description 1
229960005118 oxymorphone Drugs 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
238000010979 pH adjustment Methods 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
229940098695 palmitic acid Drugs 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
229960005489 paracetamol Drugs 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
229960000292 pectin Drugs 0.000 description 1
VOKSWYLNZZRQPF-GDIGMMSISA-N pentazocine Chemical compound C1C2=CC=C(O)C=C2[C@@]2(C)[C@@H](C)[C@@H]1N(CC=C(C)C)CC2 VOKSWYLNZZRQPF-GDIGMMSISA-N 0.000 description 1
229960005301 pentazocine Drugs 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
229960003893 phenacetin Drugs 0.000 description 1
QARVLSVVCXYDNA-UHFFFAOYSA-N phenyl bromide Natural products BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
230000002980 postoperative effect Effects 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
229960005205 prednisolone Drugs 0.000 description 1
OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
229960004618 prednisone Drugs 0.000 description 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
238000002203 pretreatment Methods 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
229960001309 procaine hydrochloride Drugs 0.000 description 1
229960003910 promethazine Drugs 0.000 description 1
YRVCHYUHISNKSG-UHFFFAOYSA-N propane-1,3-diol Chemical group OCCCO.OCCCO YRVCHYUHISNKSG-UHFFFAOYSA-N 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
DCBSHORRWZKAKO-UHFFFAOYSA-N rac-1-monomyristoylglycerol Chemical compound CCCCCCCCCCCCCC(=O)OCC(O)CO DCBSHORRWZKAKO-UHFFFAOYSA-N 0.000 description 1
230000036647 reaction Effects 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229940100618 rectal suppository Drugs 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
238000004064 recycling Methods 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
239000000523 sample Substances 0.000 description 1
230000035807 sensation Effects 0.000 description 1
235000019615 sensations Nutrition 0.000 description 1
235000019613 sensory perceptions of taste Nutrition 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
229960003885 sodium benzoate Drugs 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000008354 sodium chloride injection Substances 0.000 description 1
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
239000007905 soft elastic gelatin capsule Substances 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
ZNVGYHOBTCWGTO-UHFFFAOYSA-N solutin Natural products Cc1cc(O)cc2OC(C)(O)C(=O)c12 ZNVGYHOBTCWGTO-UHFFFAOYSA-N 0.000 description 1
239000012453 solvate Substances 0.000 description 1
238000000935 solvent evaporation Methods 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000012177 spermaceti Substances 0.000 description 1
229940084106 spermaceti Drugs 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
229960004274 stearic acid Drugs 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000007939 sustained release tablet Substances 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
230000035923 taste sensation Effects 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000012360 testing method Methods 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
229940033663 thimerosal Drugs 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000009466 transformation Effects 0.000 description 1
230000000472 traumatic effect Effects 0.000 description 1
229960002622 triacetin Drugs 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000007762 w/o emulsion Substances 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
239000008136 water-miscible vehicle Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA359,623A 1976-06-03 1980-09-05 Cetals de 4-amino-4-arylcyclohexanones Expired CA1105938A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA359,623A CA1105938A (fr)	1976-06-03	1980-09-05	Cetals de 4-amino-4-arylcyclohexanones

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US05/692,589 US4065573A (en)	1976-06-03	1976-06-03	4-Amino-4-phenylcyclohexanone ketal compositions and process of use
US692,589		1976-06-03
CA278,494A CA1093553A (fr)	1976-06-03	1977-05-16	Traduction non-disponible
CA359,623A CA1105938A (fr)	1976-06-03	1980-09-05	Cetals de 4-amino-4-arylcyclohexanones

Publications (1)

Publication Number	Publication Date
CA1105938A true CA1105938A (fr)	1981-07-28

Family

ID=27165081

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA359,623A Expired CA1105938A (fr)	1976-06-03	1980-09-05	Cetals de 4-amino-4-arylcyclohexanones

Country Status (1)

Country	Link
CA (1)	CA1105938A (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US11344510B2 (en)	2019-12-26	2022-05-31	Gilgamesh Pharmaceuticals, Inc.	Arylcyclohexylamine derivatives and their use in the treatment of psychiatric disorders
US11440879B2 (en)	2020-02-18	2022-09-13	Gilgamesh Pharmaceuticals, Inc.	Methods of treating mood disorders
US12129234B1 (en)	2023-08-03	2024-10-29	Gilgamesh Pharmaceuticals, Inc.	Crystalline salts of N-ethyl-(5-fluoro-1H-indol-3-yl)-N-methylethan-1-amine
US12157722B1 (en)	2023-08-03	2024-12-03	Gilgamesh Pharmaceuticals, Inc.	Crystalline hydrochloride salts of N-ethyl-2-(5-fluoro-1H-indol-3-yl)-N-methylethan-1-amine

1980
- 1980-09-05 CA CA359,623A patent/CA1105938A/fr not_active Expired

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US11344510B2 (en)	2019-12-26	2022-05-31	Gilgamesh Pharmaceuticals, Inc.	Arylcyclohexylamine derivatives and their use in the treatment of psychiatric disorders
US11440879B2 (en)	2020-02-18	2022-09-13	Gilgamesh Pharmaceuticals, Inc.	Methods of treating mood disorders
US12129234B1 (en)	2023-08-03	2024-10-29	Gilgamesh Pharmaceuticals, Inc.	Crystalline salts of N-ethyl-(5-fluoro-1H-indol-3-yl)-N-methylethan-1-amine
US12157722B1 (en)	2023-08-03	2024-12-03	Gilgamesh Pharmaceuticals, Inc.	Crystalline hydrochloride salts of N-ethyl-2-(5-fluoro-1H-indol-3-yl)-N-methylethan-1-amine
US12180158B1 (en)	2023-08-03	2024-12-31	Gilgamesh Pharmaceuticals, Inc.	Crystalline fumarate salts of n-ethyl-2-(5-fluoro-1H-indol-3-yl)-n-methylethan-1-amine

Legal Events

Date	Code	Title	Description
1998-07-28	MKEX	Expiry

Publication	Publication Date	Title
CA1093553A (fr)	1981-01-13	Traduction non-disponible
US4366172A (en)	1982-12-28	4-Amino-cyclohexanols, their pharmaceutical compositions and methods of use
KR960015003B1 (ko)	1996-10-23	N-(피리디닐)-1h-인돌-i-아민, 이의 제조방법 및 이를 함유하는 약제학적 조성물
JPS60109558A (ja)	1985-06-15	スルフアメ−トおよび医薬としてのその用途
JPS6059907B2 (ja)	1985-12-27	ピロリジン誘導体
US4113866A (en)	1978-09-12	Analgetic compounds, compositions and process of treatment
CA1161853A (fr)	1984-02-07	N-alkyle inferieur 3-phenoxy-1-azetidine- carboxamides
US4115589A (en)	1978-09-19	Compounds, compositions and method of use
NZ239267A (en)	1994-05-26	3-substituted piperidine derivatives and pharmaceutical compositions
US4166120A (en)	1979-08-28	Analgesic and tranquilizing benzoylpropyl-spiro[dihydrobenzofuran]piperidines and pyrrolidines
CA2077098A1 (fr)	1993-03-01	Derives du benzopyrane
CA1100516A (fr)	1981-05-05	Traduction non-disponible
AU647178B2 (en)	1994-03-17	10(1-hydroxyethyl)-11-oxo-1-azatricyclo(7.2.0.0.3.8)undec-2- ene-2-carboxylic acid esters and a process for preparing thereof
US4460604A (en)	1984-07-17	4-Amino-4-aryl-cyclohexanones
DE3854981T2 (de)	1996-09-05	1-Pyrrolidinacetamid-Derivate und ihre Verwendung
CH630629A5 (fr)	1982-06-30	Derives de la morphine, leur procede de preparation et leur application comme medicament.
IE860522L (en)	1986-08-28	3-aryloxy azetidine carboxamides
US4447454A (en)	1984-05-08	Analgetic compounds, compositions and process of treatment
US4180584A (en)	1979-12-25	4-Pyrrolidino-cyclohexanone ketals
DE3888811T2 (de)	1994-09-29	Tricyclische Carbamate, Verfahren zu ihrer Herstellung und ihre therapeutische Verwendung.
Lednicer et al.	1981	4-Aryl-4-aminocyclohexanones and their derivatives, a novel class of analgesics. 3. M-hydroxyphenyl derivatives
US4585785A (en)	1986-04-29	Cis and trans-3-aryloxy-4-hydroxypyrrolidines used as anti-arrhythmics
JPS5935387B2 (ja)	1984-08-28	３−アミノ−２−ヒドロキシプロパンのジ−置換フエノ−ルエ−テル類、その製法ならびに医薬用途
IE58121B1 (en)	1993-07-14	1,3-Disubstituted piperdine compounds as neuroleptic agents
DE2241027A1 (de)	1973-03-01	Verfahren zur herstellung neuer heterocyclischer verbindungen