OA11672A - New esters derived from substituted phenyl-cyclohexyl compounds. - Google Patents

New esters derived from substituted phenyl-cyclohexyl compounds. Download PDF

Info

Publication number: OA11672A
Authority: OA; OAPI
Prior art keywords: phenyl; dimethylaminomethyl; compound; cyclohexyl; hydroxy
Prior art date: 1998-11-06

Application number

OA1200100111A

Other languages

English (en)

Inventor

Maria Chalaux Freixa

Juan Carlos Del Castillo Nieto

Elisabet De Ramon Amat

Joan Huguet Clotet

Marisabel Mourelle Mancini

Original Assignee

Vita Invest Sa

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.)

1998-11-06

Filing date

1999-11-04

Publication date

2005-01-12

1999-11-04 Application filed by Vita Invest Sa filed Critical Vita Invest Sa

2005-01-12 Publication of OA11672A publication Critical patent/OA11672A/en

Links

150000002148 esters Chemical class 0.000 title abstract description 10
125000004351 phenylcyclohexyl group Chemical group C1(=CC=CC=C1)C1(CCCCC1)* 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 24
238000000034 method Methods 0.000 claims abstract description 18
230000008569 process Effects 0.000 claims abstract description 14
239000003814 drug Substances 0.000 claims abstract description 9
229940079593 drug Drugs 0.000 claims abstract description 8
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical group C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
239000012442 inert solvent Substances 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 2
230000003287 optical effect Effects 0.000 claims description 2
230000001737 promoting effect Effects 0.000 claims description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
230000005494 condensation Effects 0.000 claims 1
238000009833 condensation Methods 0.000 claims 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims 1
150000003839 salts Chemical class 0.000 claims 1
TVYLLZQTGLZFBW-ZBFHGGJFSA-N (R,R)-tramadol Chemical compound COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-ZBFHGGJFSA-N 0.000 abstract description 17
229960004380 tramadol Drugs 0.000 abstract description 17
TVYLLZQTGLZFBW-GOEBONIOSA-N tramadol Natural products COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GOEBONIOSA-N 0.000 abstract description 17
231100000419 toxicity Toxicity 0.000 abstract description 6
230000001988 toxicity Effects 0.000 abstract description 6
230000000202 analgesic effect Effects 0.000 abstract 2
230000000694 effects Effects 0.000 description 14
101150041968 CDC13 gene Proteins 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 9
239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
206010022998 Irritability Diseases 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 6
-1 methoxyl group Chemical group 0.000 description 6
UWJUQVWARXYRCG-UHFFFAOYSA-N o-desmethyltramadol Chemical compound CN(C)CC1CCCCC1(O)C1=CC=CC(O)=C1 UWJUQVWARXYRCG-UHFFFAOYSA-N 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
BDPAJJIAIBKWER-UHFFFAOYSA-N n,n-dimethyl-1-(2-phenylcyclohexyl)methanamine Chemical compound CN(C)CC1CCCCC1C1=CC=CC=C1 BDPAJJIAIBKWER-UHFFFAOYSA-N 0.000 description 3
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
RGXFLYSKRVEBMO-UHFFFAOYSA-N 3-[2-[(dimethylamino)methyl]cyclohexen-1-yl]phenol Chemical compound C1CCCC(CN(C)C)=C1C1=CC=CC(O)=C1 RGXFLYSKRVEBMO-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
206010010774 Constipation Diseases 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
235000013305 food Nutrition 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229960002009 naproxen Drugs 0.000 description 2
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
230000000241 respiratory effect Effects 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
238000005303 weighing Methods 0.000 description 2
DSGKWFGEUBCEIE-UHFFFAOYSA-N (2-carbonochloridoylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1C(Cl)=O DSGKWFGEUBCEIE-UHFFFAOYSA-N 0.000 description 1
IOZUASLAORDSIM-UHFFFAOYSA-N (2-carbonochloridoylphenyl) n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OC1=CC=CC=C1C(Cl)=O IOZUASLAORDSIM-UHFFFAOYSA-N 0.000 description 1
DQCVAPIWYRYMBS-UHFFFAOYSA-N 3-[3-[2-[(dimethylamino)methyl]cyclohexen-1-yl]phenyl]-2-hydroxybenzoic acid Chemical compound C1CCCC(CN(C)C)=C1C1=CC=CC(C=2C(=C(C(O)=O)C=CC=2)O)=C1 DQCVAPIWYRYMBS-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
206010012335 Dependence Diseases 0.000 description 1
206010060800 Hot flush Diseases 0.000 description 1
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 1
229940127450 Opioid Agonists Drugs 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
229920005372 Plexiglas® Polymers 0.000 description 1
HPUAIJLEUZEGSX-UHFFFAOYSA-N [3-[2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenyl] 2-[4-(2-methylpropyl)phenyl]propanoate Chemical compound C1=CC(CC(C)C)=CC=C1C(C)C(=O)OC1=CC=CC(C2(O)C(CCCC2)CN(C)C)=C1 HPUAIJLEUZEGSX-UHFFFAOYSA-N 0.000 description 1
RRSATROXEHXOFS-UHFFFAOYSA-N [3-[2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenyl] 5-benzoyl-2,3-dihydro-1h-pyrrolizine-1-carboxylate Chemical compound CN(C)CC1CCCCC1(O)C1=CC=CC(OC(=O)C2C=3N(C(=CC=3)C(=O)C=3C=CC=CC=3)CC2)=C1 RRSATROXEHXOFS-UHFFFAOYSA-N 0.000 description 1
YYJQRMSWFYCKPC-UHFFFAOYSA-N [3-[2-[(dimethylamino)methyl]cyclohexen-1-yl]phenyl] 2-(dimethylcarbamoyloxy)benzoate Chemical compound C1CCCC(CN(C)C)=C1C1=CC=CC(OC(=O)C=2C(=CC=CC=2)OC(=O)N(C)C)=C1 YYJQRMSWFYCKPC-UHFFFAOYSA-N 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
230000006378 damage Effects 0.000 description 1
235000019439 ethyl acetate Nutrition 0.000 description 1
239000000284 extract Substances 0.000 description 1
230000008570 general process Effects 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
229910052740 iodine Inorganic materials 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
OZWKMVRBQXNZKK-UHFFFAOYSA-N ketorolac Chemical compound OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 description 1
229960004752 ketorolac Drugs 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 description 1
239000003402 opiate agonist Substances 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
239000002831 pharmacologic agent Substances 0.000 description 1
239000004926 polymethyl methacrylate Substances 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
230000035900 sweating Effects 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
231100000041 toxicology testing Toxicity 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/26—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
- C07C271/42—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/44—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/26—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C219/28—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton having amino groups bound to acyclic carbon atoms of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/26—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C219/28—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton having amino groups bound to acyclic carbon atoms of the carbon skeleton
- C07C219/30—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton having amino groups bound to acyclic carbon atoms of the carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Biomedical Technology (AREA)
Public Health (AREA)
Pain & Pain Management (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

OA1200100111A 1998-11-06 1999-11-04 New esters derived from substituted phenyl-cyclohexyl compounds. OA11672A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
ES009802329A ES2141688B1 (es)	1998-11-06	1998-11-06	Nuevos esteres derivados de compuestos fenil-ciclohexil sustituidos.

Publications (1)

Publication Number	Publication Date
OA11672A true OA11672A (en)	2005-01-12

Family

ID=8305698

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200100111A OA11672A (en)	1998-11-06	1999-11-04	New esters derived from substituted phenyl-cyclohexyl compounds.

Country Status (39)

Country	Link
US (1)	US6455585B1 (is)
EP (3)	EP1219623B1 (is)
JP (1)	JP2002529442A (is)
KR (1)	KR100453613B1 (is)
CN (1)	CN1176902C (is)
AP (1)	AP1222A (is)
AT (3)	ATE257817T1 (is)
AU (1)	AU755681B2 (is)
BG (1)	BG105556A (is)
BR (1)	BR9915727A (is)
CA (1)	CA2349245A1 (is)
CR (1)	CR6368A (is)
CU (1)	CU23006A3 (is)
CZ (1)	CZ20011500A3 (is)
DE (3)	DE69914229T2 (is)
DK (3)	DK1219594T3 (is)
EA (1)	EA003742B1 (is)
EE (1)	EE200100246A (is)
ES (4)	ES2141688B1 (is)
GE (1)	GEP20033116B (is)
HR (1)	HRP20010412B1 (is)
HU (1)	HUP0104218A3 (is)
ID (1)	ID29017A (is)
IL (1)	IL142592A0 (is)
IS (1)	IS5934A (is)
MA (1)	MA26765A1 (is)
MX (1)	MXPA01004432A (is)
NO (1)	NO20012234L (is)
NZ (1)	NZ511739A (is)
OA (1)	OA11672A (is)
PL (1)	PL347492A1 (is)
PT (3)	PT1127871E (is)
SI (3)	SI1127871T1 (is)
SK (1)	SK284068B6 (is)
TR (3)	TR200200415T2 (is)
UA (1)	UA59477C2 (is)
WO (1)	WO2000027799A1 (is)
YU (1)	YU29601A (is)
ZA (1)	ZA200104026B (is)

Families Citing this family (39)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES2160534B1 (es) *	1999-12-30	2002-04-16	Vita Invest Sa	Nuevos esteres derivados de (rr,ss)-2-hidroxibenzoato de 3-(2-dimetilaminometil-1-hidroxiciclohexil) fenilo.
DE10049483A1 (de) *	2000-09-29	2002-05-02	Gruenenthal Gmbh	Substituierte 1-Aminobutan-3-ol-Derivate
US7776314B2 (en)	2002-06-17	2010-08-17	Grunenthal Gmbh	Abuse-proofed dosage system
WO2004026291A1 (en) *	2002-08-28	2004-04-01	Shuyi Zhang	Oral formulations of ibuprofen and tramadol, methods and preparation thereof
ATE391498T1 (de) *	2002-11-22	2008-04-15	Gruenenthal Gmbh	Verwendung von (1rs,3rs,6rs)-6- dimethylaminomethyl-1-(3-methoxy-phenyl)- cyclohexan-1,3-diol zur behandlung von entzündungsschmerz
US20040248979A1 (en) *	2003-06-03	2004-12-09	Dynogen Pharmaceuticals, Inc.	Method of treating lower urinary tract disorders
DE102005005446A1 (de)	2005-02-04	2006-08-10	Grünenthal GmbH	Bruchfeste Darreichungsformen mit retardierter Freisetzung
US20070048228A1 (en)	2003-08-06	2007-03-01	Elisabeth Arkenau-Maric	Abuse-proofed dosage form
DE10361596A1 (de)	2003-12-24	2005-09-29	Grünenthal GmbH	Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform
DE10336400A1 (de)	2003-08-06	2005-03-24	Grünenthal GmbH	Gegen Missbrauch gesicherte Darreichungsform
DE102004032051A1 (de)	2004-07-01	2006-01-19	Grünenthal GmbH	Verfahren zur Herstellung einer gegen Missbrauch gesicherten, festen Darreichungsform
US8075872B2 (en)	2003-08-06	2011-12-13	Gruenenthal Gmbh	Abuse-proofed dosage form
DE102004032049A1 (de)	2004-07-01	2006-01-19	Grünenthal GmbH	Gegen Missbrauch gesicherte, orale Darreichungsform
DE102004034619A1 (de) *	2004-07-16	2006-02-23	Grünenthal GmbH	Substituierte Aminoverbindungen als 5-HT/NA Uptakehemmer
DE102005005449A1 (de)	2005-02-04	2006-08-10	Grünenthal GmbH	Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform
DE102007011485A1 (de)	2007-03-07	2008-09-11	Grünenthal GmbH	Darreichungsform mit erschwertem Missbrauch
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1998
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Also Published As

Publication number	Publication date
ZA200104026B (en)	2002-05-17
CU23006A3 (es)	2004-12-17
EP1127871B1 (en)	2003-09-10
DE69914231D1 (de)	2004-02-19
ES2141688B1 (es)	2001-02-01
ES2141688A1 (es)	2000-05-16
HUP0104218A3 (en)	2002-11-28
ES2213732T3 (es)	2004-09-01
MXPA01004432A (es)	2002-09-18
PL347492A1 (en)	2002-04-08
HUP0104218A2 (hu)	2002-03-28
EA003742B1 (ru)	2003-08-28
IL142592A0 (en)	2002-03-10
SI1219594T1 (en)	2004-06-30
KR100453613B1 (ko)	2004-10-20
CN1176902C (zh)	2004-11-24
GEP20033116B (en)	2003-11-25
ATE257817T1 (de)	2004-01-15
NZ511739A (en)	2002-11-26
BG105556A (en)	2001-12-29
BR9915727A (pt)	2001-09-04
CA2349245A1 (en)	2000-05-18
SI1219623T1 (en)	2004-06-30
KR20010080942A (ko)	2001-08-25
DE69914229D1 (de)	2004-02-19
EP1219623B1 (en)	2004-01-14
ES2213731T3 (es)	2004-09-01
CZ20011500A3 (cs)	2001-09-12
IS5934A (is)	2001-05-03
DK1219594T3 (da)	2004-04-19
WO2000027799A1 (es)	2000-05-18
ID29017A (id)	2001-07-26
EE200100246A (et)	2002-12-16
AU755681B2 (en)	2002-12-19
UA59477C2 (uk)	2003-09-15
TR200101160T2 (tr)	2002-01-21
EP1127871A1 (en)	2001-08-29
EP1219623A1 (en)	2002-07-03
PT1219623E (pt)	2004-04-30
DE69914231T2 (de)	2004-11-11
PT1219594E (pt)	2004-04-30
EP1219594A1 (en)	2002-07-03
AP1222A (en)	2003-11-06
CR6368A (es)	2002-04-08
ATE249418T1 (de)	2003-09-15
DK1219623T3 (da)	2004-04-19
AU1047300A (en)	2000-05-29
EP1219594B1 (en)	2004-01-14
DE69911235D1 (de)	2003-10-16
EA200100476A1 (ru)	2002-02-28
MA26765A1 (fr)	2004-12-20
DE69914229T2 (de)	2004-12-09
SI1127871T1 (en)	2004-02-29
HRP20010412A2 (en)	2002-12-31
JP2002529442A (ja)	2002-09-10
US6455585B1 (en)	2002-09-24
PT1127871E (pt)	2003-12-31
CN1325377A (zh)	2001-12-05
TR200200416T2 (tr)	2003-01-21
HRP20010412B1 (en)	2004-04-30
NO20012234D0 (no)	2001-05-04
ATE257837T1 (de)	2004-01-15
DK1127871T3 (da)	2003-11-24
TR200200415T2 (tr)	2002-06-21
DE69911235T2 (de)	2004-07-01
ES2207298T3 (es)	2004-05-16
NO20012234L (no)	2001-05-04
YU29601A (sh)	2003-04-30
SK284068B6 (sk)	2004-09-08
SK5842001A3 (en)	2001-12-03

Publication	Publication Date	Title
OA11672A (en)	2005-01-12	New esters derived from substituted phenyl-cyclohexyl compounds.
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CA2999367A1 (en)	2017-03-30	Prodrugs of gamma-hydroxybutyric acid, compositions and uses thereof
WO2017049470A1 (en)	2017-03-30	Prodrugs of gamma-hydroxybutyric acid, compositions and uses thereof
CA2584610A1 (en)	2006-04-27	Novel dicarboxylic acid derivatives
JPH02306947A (ja)	1990-12-20	キラルβ―アミノ酸の製造方法
JP3231775B2 (ja)	2001-11-26	心循環器系に作用する２−アミノ−１，２，３，４−テトラヒドロナフタレン誘導体、それらを製造する方法、及びそれらを含む医薬組成物
JP2861274B2 (ja)	1999-02-24	アミノケトン誘導体
JPH02121953A (ja)	1990-05-09	シクロアルキル置換４―アミノフェニル誘導体およびその製造方法