NO328672B1 - Substituerte 4-aminocykloheksanolderivater, legemiddel inneholdende minst en slik forbindelse, anvendelse av forbindelsen samt fremgangsmate for fremstilling derav - Google Patents
Substituerte 4-aminocykloheksanolderivater, legemiddel inneholdende minst en slik forbindelse, anvendelse av forbindelsen samt fremgangsmate for fremstilling derav Download PDFInfo
- Publication number
- NO328672B1 NO328672B1 NO20040162A NO20040162A NO328672B1 NO 328672 B1 NO328672 B1 NO 328672B1 NO 20040162 A NO20040162 A NO 20040162A NO 20040162 A NO20040162 A NO 20040162A NO 328672 B1 NO328672 B1 NO 328672B1
- Authority
- NO
- Norway
- Prior art keywords
- benzyl
- dimethylamino
- optionally
- substituted
- unsubstituted
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 46
- IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical class NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 title claims description 33
- 239000003814 drug Chemical class 0.000 title claims description 24
- 229940079593 drug Drugs 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 89
- 150000003839 salts Chemical class 0.000 claims description 40
- 125000006239 protecting group Chemical group 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 28
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 208000002193 Pain Diseases 0.000 claims description 15
- -1 4-substituted 4- aminocyclohexanone Chemical class 0.000 claims description 14
- 150000007513 acids Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000003153 chemical reaction reagent Substances 0.000 claims description 12
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 10
- 150000004677 hydrates Chemical class 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 239000012453 solvate Substances 0.000 claims description 10
- 239000013543 active substance Substances 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 230000036407 pain Effects 0.000 claims description 8
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
- 230000003444 anaesthetic effect Effects 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001979 organolithium group Chemical group 0.000 claims description 6
- 125000002524 organometallic group Chemical group 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- HLPJHVZSARAGNF-UHFFFAOYSA-N 1-(1-benzofuran-2-yl)-4-benzyl-4-(dimethylamino)cyclohexan-1-ol Chemical compound C1CC(O)(C=2OC3=CC=CC=C3C=2)CCC1(N(C)C)CC1=CC=CC=C1 HLPJHVZSARAGNF-UHFFFAOYSA-N 0.000 claims description 4
- QZAZJLODHHLCBN-UHFFFAOYSA-N 4-(dimethylamino)-4-[(4-fluorophenyl)methyl]-1-(1-phenylethyl)cyclohexan-1-ol Chemical compound CN(C1(CCC(CC1)(O)C(C)C1=CC=CC=C1)CC1=CC=C(C=C1)F)C QZAZJLODHHLCBN-UHFFFAOYSA-N 0.000 claims description 4
- IKIQCUTWIGOISN-UHFFFAOYSA-N 4-benzyl-4-(dimethylamino)-1-(2-phenylethyl)cyclohexan-1-ol Chemical compound C1CC(O)(CCC=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC=C1 IKIQCUTWIGOISN-UHFFFAOYSA-N 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
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- 208000004880 Polyuria Diseases 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 230000035619 diuresis Effects 0.000 claims description 4
- 206010015037 epilepsy Diseases 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 208000004296 neuralgia Diseases 0.000 claims description 4
- 208000021722 neuropathic pain Diseases 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- DPWXGWFFRSWLGI-UHFFFAOYSA-N 1-(1-benzothiophen-2-yl)-4-benzyl-4-(dimethylamino)cyclohexan-1-ol Chemical compound C1CC(O)(C=2SC3=CC=CC=C3C=2)CCC1(N(C)C)CC1=CC=CC=C1 DPWXGWFFRSWLGI-UHFFFAOYSA-N 0.000 claims description 3
- HWVSCKZGKCUMDZ-UHFFFAOYSA-N 1-(1-benzothiophen-3-yl)-4-benzyl-4-(dimethylamino)cyclohexan-1-ol Chemical compound C1CC(O)(C=2C3=CC=CC=C3SC=2)CCC1(N(C)C)CC1=CC=CC=C1 HWVSCKZGKCUMDZ-UHFFFAOYSA-N 0.000 claims description 3
- FTCXWNUJMSGUKP-UHFFFAOYSA-N 1-amino-4-oxocyclohexane-1-carbonitrile Chemical class N#CC1(N)CCC(=O)CC1 FTCXWNUJMSGUKP-UHFFFAOYSA-N 0.000 claims description 3
- MWXQPXJCCYOMML-UHFFFAOYSA-N 1-benzyl-4-(dimethylamino)-4-[(3-fluorophenyl)methyl]cyclohexan-1-ol Chemical compound C1CC(O)(CC=2C=CC=CC=2)CCC1(N(C)C)CC1=CC=CC(F)=C1 MWXQPXJCCYOMML-UHFFFAOYSA-N 0.000 claims description 3
- KIPQQODCTKSBIL-UHFFFAOYSA-N 4-benzyl-1-(1-phenylethyl)-4-pyrrolidin-1-ylcyclohexan-1-ol Chemical compound C(C1=CC=CC=C1)C1(CCC(CC1)(O)C(C)C1=CC=CC=C1)N1CCCC1 KIPQQODCTKSBIL-UHFFFAOYSA-N 0.000 claims description 3
- AZXIFXSGZIQDQE-UHFFFAOYSA-N 4-benzyl-4-(dimethylamino)-1-(1-methylindol-2-yl)cyclohexan-1-ol Chemical compound C1CC(O)(C=2N(C3=CC=CC=C3C=2)C)CCC1(N(C)C)CC1=CC=CC=C1 AZXIFXSGZIQDQE-UHFFFAOYSA-N 0.000 claims description 3
- DEVVWYCTPQSONW-UHFFFAOYSA-N 4-benzyl-4-(dimethylamino)-1-[(2-fluorophenyl)methyl]cyclohexan-1-ol Chemical compound C1CC(O)(CC=2C(=CC=CC=2)F)CCC1(N(C)C)CC1=CC=CC=C1 DEVVWYCTPQSONW-UHFFFAOYSA-N 0.000 claims description 3
- RFANFAMERSJCMR-UHFFFAOYSA-N 4-benzyl-4-(dimethylamino)-1-[(3-fluorophenyl)methyl]cyclohexan-1-ol Chemical compound C1CC(O)(CC=2C=C(F)C=CC=2)CCC1(N(C)C)CC1=CC=CC=C1 RFANFAMERSJCMR-UHFFFAOYSA-N 0.000 claims description 3
- NKBRPMLEGMZKCU-UHFFFAOYSA-N 4-benzyl-4-(dimethylamino)-1-[(4-fluorophenyl)methyl]cyclohexan-1-ol Chemical compound C1CC(O)(CC=2C=CC(F)=CC=2)CCC1(N(C)C)CC1=CC=CC=C1 NKBRPMLEGMZKCU-UHFFFAOYSA-N 0.000 claims description 3
- YEPPMVHLAVYETM-UHFFFAOYSA-N CN(C1(CCC(CC1)(O)C(C)C1=CC=CC=C1)CC1=C(C=CC=C1)F)C Chemical compound CN(C1(CCC(CC1)(O)C(C)C1=CC=CC=C1)CC1=C(C=CC=C1)F)C YEPPMVHLAVYETM-UHFFFAOYSA-N 0.000 claims description 3
- SAFYTDNZDKDJPB-UHFFFAOYSA-N CN(C1(CCC(CC1)(O)C(C)C1=CC=CC=C1)CC1=CC(=CC=C1)F)C Chemical compound CN(C1(CCC(CC1)(O)C(C)C1=CC=CC=C1)CC1=CC(=CC=C1)F)C SAFYTDNZDKDJPB-UHFFFAOYSA-N 0.000 claims description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
- 206010012335 Dependence Diseases 0.000 claims description 3
- 206010012735 Diarrhoea Diseases 0.000 claims description 3
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 3
- 206010046543 Urinary incontinence Diseases 0.000 claims description 3
- 230000001154 acute effect Effects 0.000 claims description 3
- 208000005298 acute pain Diseases 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 125000005219 aminonitrile group Chemical group 0.000 claims description 3
- 230000000954 anitussive effect Effects 0.000 claims description 3
- 229940124584 antitussives Drugs 0.000 claims description 3
- DCZFGQYXRKMVFG-UHFFFAOYSA-N cyclohexane-1,4-dione Chemical compound O=C1CCC(=O)CC1 DCZFGQYXRKMVFG-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 230000008991 intestinal motility Effects 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 230000002981 neuropathic effect Effects 0.000 claims description 3
- 239000002664 nootropic agent Substances 0.000 claims description 3
- 230000001777 nootropic effect Effects 0.000 claims description 3
- 235000015816 nutrient absorption Nutrition 0.000 claims description 3
- 230000009278 visceral effect Effects 0.000 claims description 3
- 208000009935 visceral pain Diseases 0.000 claims description 3
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims description 2
- XNASBXIWFHODQU-UHFFFAOYSA-N 4-benzyl-4-(dimethylamino)-1-[2-(2-fluorophenyl)ethyl]cyclohexan-1-ol Chemical compound C1CC(O)(CCC=2C(=CC=CC=2)F)CCC1(N(C)C)CC1=CC=CC=C1 XNASBXIWFHODQU-UHFFFAOYSA-N 0.000 claims description 2
- LIDIVDQKVAMPMK-UHFFFAOYSA-N 4-benzyl-4-(dimethylamino)-1-[2-(3-fluorophenyl)ethyl]cyclohexan-1-ol Chemical compound C1CC(O)(CCC=2C=C(F)C=CC=2)CCC1(N(C)C)CC1=CC=CC=C1 LIDIVDQKVAMPMK-UHFFFAOYSA-N 0.000 claims description 2
- 208000019901 Anxiety disease Diseases 0.000 claims description 2
- 206010006895 Cachexia Diseases 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 206010020772 Hypertension Diseases 0.000 claims description 2
- 206010048865 Hypoacusis Diseases 0.000 claims description 2
- 208000001953 Hypotension Diseases 0.000 claims description 2
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- 208000008589 Obesity Diseases 0.000 claims description 2
- 208000003251 Pruritus Diseases 0.000 claims description 2
- 206010039966 Senile dementia Diseases 0.000 claims description 2
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 2
- 208000009205 Tinnitus Diseases 0.000 claims description 2
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- 230000001773 anti-convulsant effect Effects 0.000 claims description 2
- 239000001961 anticonvulsive agent Substances 0.000 claims description 2
- 229960003965 antiepileptics Drugs 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 2
- 238000011260 co-administration Methods 0.000 claims description 2
- 208000010877 cognitive disease Diseases 0.000 claims description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 2
- 206010061428 decreased appetite Diseases 0.000 claims description 2
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 230000036543 hypotension Effects 0.000 claims description 2
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- 239000003158 myorelaxant agent Substances 0.000 claims description 2
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- 208000011580 syndromic disease Diseases 0.000 claims description 2
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- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- 101100448208 Human herpesvirus 6B (strain Z29) U69 gene Proteins 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 240
- 239000000243 solution Substances 0.000 description 88
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 55
- 238000001816 cooling Methods 0.000 description 37
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 33
- 235000011152 sodium sulphate Nutrition 0.000 description 33
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- 239000012043 crude product Substances 0.000 description 13
- SOQQQHJQTOJEOW-UHFFFAOYSA-N 4-benzyl-4-(dimethylamino)cyclohexan-1-one Chemical compound C=1C=CC=CC=1CC1(N(C)C)CCC(=O)CC1 SOQQQHJQTOJEOW-UHFFFAOYSA-N 0.000 description 12
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 12
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- OUTILEHLSPAZIN-UHFFFAOYSA-M magnesium;ethylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]CC1=CC=CC=C1 OUTILEHLSPAZIN-UHFFFAOYSA-M 0.000 description 8
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- 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 7
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- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
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Classifications
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- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/42—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/44—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton bound to carbon atoms of the same ring or condensed ring system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
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- C07D333/58—Radicals substituted by nitrogen atoms
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
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- Hospice & Palliative Care (AREA)
- Diabetes (AREA)
- Vascular Medicine (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Toxicology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10135635A DE10135635A1 (de) | 2001-07-17 | 2001-07-17 | Analgetische substituierte 4-Aminocyclohexanolderivate |
| DE10135637A DE10135637A1 (de) | 2001-07-17 | 2001-07-17 | Substituierte 4-Aminocyclohexanolderivate |
| PCT/EP2002/007849 WO2003008371A1 (de) | 2001-07-17 | 2002-07-15 | Substituierte 4-aminocyclohexanolderivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20040162L NO20040162L (no) | 2004-03-11 |
| NO328672B1 true NO328672B1 (no) | 2010-04-19 |
Family
ID=26009751
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20040162A NO328672B1 (no) | 2001-07-17 | 2004-01-14 | Substituerte 4-aminocykloheksanolderivater, legemiddel inneholdende minst en slik forbindelse, anvendelse av forbindelsen samt fremgangsmate for fremstilling derav |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US7678834B2 (ja) |
| EP (1) | EP1406859B1 (ja) |
| JP (1) | JP4126271B2 (ja) |
| KR (1) | KR100886579B1 (ja) |
| CN (1) | CN100584819C (ja) |
| AR (1) | AR036171A1 (ja) |
| AT (1) | ATE382601T1 (ja) |
| AU (1) | AU2002328894B2 (ja) |
| BR (1) | BR0211223A (ja) |
| CA (1) | CA2453843C (ja) |
| CO (1) | CO5550425A2 (ja) |
| CY (1) | CY1107231T1 (ja) |
| DE (1) | DE50211466D1 (ja) |
| DK (1) | DK1406859T3 (ja) |
| ES (1) | ES2298389T3 (ja) |
| HK (1) | HK1065305A1 (ja) |
| HU (1) | HU229121B1 (ja) |
| IL (2) | IL159873A0 (ja) |
| MX (1) | MXPA04000272A (ja) |
| NO (1) | NO328672B1 (ja) |
| NZ (1) | NZ531112A (ja) |
| PE (1) | PE20030320A1 (ja) |
| PL (1) | PL208792B1 (ja) |
| PT (1) | PT1406859E (ja) |
| RU (1) | RU2315750C2 (ja) |
| SI (1) | SI1406859T1 (ja) |
| WO (1) | WO2003008371A1 (ja) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040186310A1 (en) * | 2001-06-22 | 2004-09-23 | Kim Keun-Sik | Process for preparation of cyclohexanol derivatives |
| JP2007204409A (ja) * | 2006-02-01 | 2007-08-16 | Sumitomo Chemical Co Ltd | アルキルベンゼン化合物の製造方法 |
| DE102006033109A1 (de) * | 2006-07-18 | 2008-01-31 | Grünenthal GmbH | Substituierte Heteroaryl-Derivate |
| EP3101018B1 (en) * | 2007-08-31 | 2019-03-06 | Purdue Pharma L.P. | Substituted-quinoxaline-type-piperidine compounds and the uses thereof |
| US20090215725A1 (en) * | 2008-02-26 | 2009-08-27 | Grunenthal Gmbh | Substituted 4-aminocyclohexane derivatives |
| AU2009228637B2 (en) * | 2008-03-27 | 2013-12-19 | Grunenthal Gmbh | (Hetero-)aryl cyclohexane derivatives |
| EP2502907B1 (de) | 2008-03-27 | 2018-08-29 | Grünenthal GmbH | Substituierte 4-Aminocyclohexan-Derivate |
| WO2010032322A1 (ja) * | 2008-09-22 | 2010-03-25 | 日清ファルマ株式会社 | 抗炎症性ペプチド |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE160007C (ja) | 1900-01-01 | |||
| FR2135883A6 (en) | 1971-04-29 | 1972-12-22 | Gryspeerdt Andre | Jacquard mechanism - using upper and lower frames carrying punched plates |
| US4115589A (en) * | 1977-05-17 | 1978-09-19 | The Upjohn Company | Compounds, compositions and method of use |
| US4366172A (en) * | 1977-09-29 | 1982-12-28 | The Upjohn Company | 4-Amino-cyclohexanols, their pharmaceutical compositions and methods of use |
| US4212878A (en) * | 1978-01-26 | 1980-07-15 | The Upjohn Company | Phenylacetamide derivative analgesics |
| US4346101A (en) * | 1980-12-08 | 1982-08-24 | The Upjohn Company | Benzamide derivative analgesics |
| FR2603612B1 (fr) * | 1986-09-05 | 1988-12-09 | Brochier Soieries J | Dispositif de variation de la densite des fils de chaine dans un metier a tisser |
| DE3924304A1 (de) | 1989-07-22 | 1991-01-31 | Bayer Ag | Neue fluorierte cyclohexanderivate, verfahren und zwischenprodukte zu deren herstellung und die verwendung der neuen fluorierten cyclohexanderivate als fungizide und zwischenprodukte |
| DE4031515C1 (ja) | 1990-08-22 | 1991-10-10 | Schroers Jacquard Papierind | |
| US5304479A (en) * | 1991-12-06 | 1994-04-19 | Diagnostic Reagents, Inc. | Phencyclidine compounds and assays for its determination |
| FR2685015B1 (fr) * | 1991-12-12 | 1994-04-01 | Staubli Verdol Sa | Attache rapide pour la liaison d'au moins un element funiculaire par rapport a l'extremite d'un cordon. |
| US5239110A (en) * | 1992-12-30 | 1993-08-24 | Sterling Winthrop, Inc. | Phenylcyclohexanol derivatives as agents for treating CNS disorders |
| FR2726011B1 (fr) | 1994-10-25 | 1996-12-20 | Staubli Sa Ets | Nouvel harnais demontable pour mecaniques jacquard |
| DE19525137C2 (de) * | 1995-07-11 | 2003-02-27 | Gruenenthal Gmbh | 6-Dimethylaminomethyl-1-phenyl-cyclohexanverbin -dungen als Zwischenprodukte zur Herstellung pharmazeutischer Wirkstoffe |
| DE19939044A1 (de) * | 1999-08-18 | 2001-03-15 | Gruenenthal Gmbh | Verwendung von Morphinanderivaten als Arzneimittel |
| DE19963175A1 (de) * | 1999-12-27 | 2001-07-12 | Gruenenthal Gmbh | Verwendung von substituierten 4-Amino-1-phenylbutan-2-ol-Verbindungen als Arzneimittel |
| IL151018A0 (en) * | 2000-03-17 | 2003-02-12 | Bristol Myers Squibb Pharma Co | Beta-amino acid derivatives as inhibitors of matrix metalloproteases and tnf-alpha |
| DE10135636A1 (de) * | 2001-07-17 | 2003-02-06 | Gruenenthal Gmbh | Substituierte 4-Aminocyclohexanole |
| DE20118363U1 (de) | 2001-11-13 | 2002-01-17 | Textilma Ag, Hergiswil | Chorbrett für Webmaschinen |
-
2002
- 2002-07-12 PE PE2002000624A patent/PE20030320A1/es not_active Application Discontinuation
- 2002-07-15 WO PCT/EP2002/007849 patent/WO2003008371A1/de active IP Right Grant
- 2002-07-15 MX MXPA04000272A patent/MXPA04000272A/es active IP Right Grant
- 2002-07-15 RU RU2004104628/04A patent/RU2315750C2/ru not_active IP Right Cessation
- 2002-07-15 AU AU2002328894A patent/AU2002328894B2/en not_active Ceased
- 2002-07-15 JP JP2003513932A patent/JP4126271B2/ja not_active Expired - Fee Related
- 2002-07-15 DK DK02764691T patent/DK1406859T3/da active
- 2002-07-15 EP EP02764691A patent/EP1406859B1/de not_active Expired - Lifetime
- 2002-07-15 DE DE50211466T patent/DE50211466D1/de not_active Expired - Lifetime
- 2002-07-15 KR KR1020047000679A patent/KR100886579B1/ko not_active IP Right Cessation
- 2002-07-15 CA CA2453843A patent/CA2453843C/en not_active Expired - Fee Related
- 2002-07-15 BR BR0211223-0A patent/BR0211223A/pt not_active Application Discontinuation
- 2002-07-15 NZ NZ531112A patent/NZ531112A/en not_active IP Right Cessation
- 2002-07-15 PT PT02764691T patent/PT1406859E/pt unknown
- 2002-07-15 AT AT02764691T patent/ATE382601T1/de active
- 2002-07-15 IL IL15987302A patent/IL159873A0/xx active IP Right Grant
- 2002-07-15 PL PL368040A patent/PL208792B1/pl unknown
- 2002-07-15 CN CN02817915A patent/CN100584819C/zh not_active Expired - Fee Related
- 2002-07-15 SI SI200230649T patent/SI1406859T1/sl unknown
- 2002-07-15 HU HU0400207A patent/HU229121B1/hu not_active IP Right Cessation
- 2002-07-15 AR ARP020102648A patent/AR036171A1/es unknown
- 2002-07-15 ES ES02764691T patent/ES2298389T3/es not_active Expired - Lifetime
-
2004
- 2004-01-13 CO CO04001678A patent/CO5550425A2/es not_active Application Discontinuation
- 2004-01-14 NO NO20040162A patent/NO328672B1/no not_active IP Right Cessation
- 2004-01-15 IL IL159873A patent/IL159873A/en not_active IP Right Cessation
- 2004-01-16 US US10/758,241 patent/US7678834B2/en not_active Expired - Fee Related
- 2004-10-13 HK HK04107856A patent/HK1065305A1/xx not_active IP Right Cessation
-
2008
- 2008-03-06 CY CY20081100257T patent/CY1107231T1/el unknown
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| MM1K | Lapsed by not paying the annual fees |