NL8800805A - Gesubstitueerde 1,3-dioxolaan en 1,3-dioxaanderivaten, werkwijzen voor de bereiding van deze derivaten en hun toepassing. - Google Patents

Gesubstitueerde 1,3-dioxolaan en 1,3-dioxaanderivaten, werkwijzen voor de bereiding van deze derivaten en hun toepassing. Download PDF

Info

Publication number: NL8800805A
Authority: NL; Netherlands
Prior art keywords: tolyl; dioxolane; formula; compound; butyl
Prior art date: 1987-04-01

Application number

NL8800805A

Other languages

English (en)

Dutch (nl)

Original Assignee

Sandoz Ag

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.)

1987-04-01

Filing date

1988-03-30

Publication date

1988-11-01

1988-03-30 Application filed by Sandoz Ag filed Critical Sandoz Ag

1988-11-01 Publication of NL8800805A publication Critical patent/NL8800805A/nl

Links

238000000034 method Methods 0.000 title claims description 11
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical class C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 title description 3
VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical class C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 39
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 11
239000000825 pharmaceutical preparation Substances 0.000 claims description 10
239000002775 capsule Substances 0.000 claims description 9
239000000839 emulsion Substances 0.000 claims description 9
206010012601 diabetes mellitus Diseases 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
KONLOUNOGLJAIE-UHFFFAOYSA-N 2-tert-butyl-2-(4-methylphenyl)-1,3-dioxolane Chemical compound C1=CC(C)=CC=C1C1(C(C)(C)C)OCCO1 KONLOUNOGLJAIE-UHFFFAOYSA-N 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
239000003472 antidiabetic agent Substances 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
229940125708 antidiabetic agent Drugs 0.000 claims description 3
239000006188 syrup Substances 0.000 claims description 3
235000020357 syrup Nutrition 0.000 claims description 3
JFSURDQTNPEVAL-UHFFFAOYSA-N 2-(1-methylcyclohexyl)-2-(4-methylphenyl)-1,3-dioxolane Chemical compound C1=CC(C)=CC=C1C1(C2(C)CCCCC2)OCCO1 JFSURDQTNPEVAL-UHFFFAOYSA-N 0.000 claims description 2
KMLAMOMPQVOCBA-UHFFFAOYSA-N 2-(1-methylcyclopropyl)-2-(4-methylphenyl)-1,3-dioxolane Chemical compound C1=CC(C)=CC=C1C1(C2(C)CC2)OCCO1 KMLAMOMPQVOCBA-UHFFFAOYSA-N 0.000 claims description 2
GVSIMOFSQGJJFE-UHFFFAOYSA-N 2-(2-adamantyl)-2-(4-methylphenyl)-1,3-dioxolane Chemical compound C12C(C3CC(CC(C1)C3)C2)C2(OCCO2)C2=CC=C(C=C2)C GVSIMOFSQGJJFE-UHFFFAOYSA-N 0.000 claims description 2
CEVJOQXUFOIJNG-UHFFFAOYSA-N 2-(2-methylpentan-2-yl)-2-(4-methylphenyl)-1,3-dioxolane Chemical compound C=1C=C(C)C=CC=1C1(C(C)(C)CCC)OCCO1 CEVJOQXUFOIJNG-UHFFFAOYSA-N 0.000 claims description 2
LUFBGYMZEQHSPV-UHFFFAOYSA-N 2-(3-ethylpentan-3-yl)-2-(4-methylphenyl)-1,3-dioxolane Chemical compound C=1C=C(C)C=CC=1C1(C(CC)(CC)CC)OCCO1 LUFBGYMZEQHSPV-UHFFFAOYSA-N 0.000 claims description 2
PUGWYZCAGAHQNO-UHFFFAOYSA-N 2-tert-butyl-2-(4-methylphenyl)-1,3-dioxane Chemical compound C1=CC(C)=CC=C1C1(C(C)(C)C)OCCCO1 PUGWYZCAGAHQNO-UHFFFAOYSA-N 0.000 claims description 2
KAQZZSGJCQCQDU-UHFFFAOYSA-N 2-tert-butyl-4,5-dimethyl-2-(4-methylphenyl)-1,3-dioxolane Chemical compound O1C(C)C(C)OC1(C(C)(C)C)C1=CC=C(C)C=C1 KAQZZSGJCQCQDU-UHFFFAOYSA-N 0.000 claims description 2
STBSQPTWFWISDM-UHFFFAOYSA-N 2-tert-butyl-4-methyl-2-(4-methylphenyl)-1,3-dioxolane Chemical compound O1C(C)COC1(C(C)(C)C)C1=CC=C(C)C=C1 STBSQPTWFWISDM-UHFFFAOYSA-N 0.000 claims description 2
ZBOOOHNXFIMWRE-UHFFFAOYSA-N 2-tert-butyl-5,5-dimethyl-2-(4-methylphenyl)-1,3-dioxane Chemical compound C1=CC(C)=CC=C1C1(C(C)(C)C)OCC(C)(C)CO1 ZBOOOHNXFIMWRE-UHFFFAOYSA-N 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
239000008187 granular material Substances 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
239000000843 powder Substances 0.000 claims description 2
ZRYUJKCBKVZXPJ-UHFFFAOYSA-N 2-(2-methylbutan-2-yl)-2-(4-methylphenyl)-1,3-dioxolane Chemical compound C=1C=C(C)C=CC=1C1(C(C)(C)CC)OCCO1 ZRYUJKCBKVZXPJ-UHFFFAOYSA-N 0.000 claims 1
229940125810 compound 20 Drugs 0.000 claims 1
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JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 claims 1
238000007911 parenteral administration Methods 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
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239000007788 liquid Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000001154 acute effect Effects 0.000 description 3
230000003178 anti-diabetic effect Effects 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
230000001684 chronic effect Effects 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
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239000000454 talc Substances 0.000 description 3
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150000000093 1,3-dioxanes Chemical class 0.000 description 2
ZYWGAHRBGCEFAO-UHFFFAOYSA-N 2,2-dimethyl-1-(4-methylphenyl)propan-1-one Chemical compound CC1=CC=C(C(=O)C(C)(C)C)C=C1 ZYWGAHRBGCEFAO-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
235000021355 Stearic acid Nutrition 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000013543 active substance Substances 0.000 description 2
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150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
229940079593 drug Drugs 0.000 description 2
235000013305 food Nutrition 0.000 description 2
WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
239000008101 lactose Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 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
239000000546 pharmaceutical excipient Substances 0.000 description 2
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
239000001267 polyvinylpyrrolidone Substances 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
238000010561 standard procedure Methods 0.000 description 2
239000008117 stearic acid Substances 0.000 description 2
ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 2
229960001052 streptozocin Drugs 0.000 description 2
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125000003944 tolyl group Chemical group 0.000 description 2
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210000003462 vein Anatomy 0.000 description 2
GLIVXMCIDJSIMJ-UHFFFAOYSA-N (1-methylcyclopropyl)-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)C1(C)CC1 GLIVXMCIDJSIMJ-UHFFFAOYSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
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CUBXMCHSJORTEN-UHFFFAOYSA-N 2,2-diethyl-1-(4-methylphenyl)butan-1-one Chemical compound C1(=CC=C(C=C1)C(=O)C(CC)(CC)CC)C CUBXMCHSJORTEN-UHFFFAOYSA-N 0.000 description 1
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FDSAYCYOKLMSHG-UHFFFAOYSA-N 2,2-dimethyl-1-(4-methylphenyl)pentan-1-one Chemical compound C1(=CC=C(C=C1)C(=O)C(CCC)(C)C)C FDSAYCYOKLMSHG-UHFFFAOYSA-N 0.000 description 1
WGTYXBCLGNWBEN-UHFFFAOYSA-N 2-(4-methylphenyl)-1,3-dioxolane Chemical compound C1=CC(C)=CC=C1C1OCCO1 WGTYXBCLGNWBEN-UHFFFAOYSA-N 0.000 description 1
UWWGSXYTVPACKO-UHFFFAOYSA-N 2-tert-butyl-2-(3-methylphenyl)-1,3-dioxolane Chemical compound CC1=CC=CC(C2(OCCO2)C(C)(C)C)=C1 UWWGSXYTVPACKO-UHFFFAOYSA-N 0.000 description 1
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 1
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ZSJLQEPLLKMAKR-UHFFFAOYSA-N Streptozotocin Natural products O=NN(C)C(=O)NC1C(O)OC(CO)C(O)C1O ZSJLQEPLLKMAKR-UHFFFAOYSA-N 0.000 description 1
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238000010521 absorption reaction Methods 0.000 description 1
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 1
150000001266 acyl halides Chemical class 0.000 description 1
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
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239000012298 atmosphere Substances 0.000 description 1
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TXNJMRAUGLOGEY-UHFFFAOYSA-N bis[4-methyl-3-(1-methylcyclohexyl)phenyl]methanone Chemical compound CC1(CCCCC1)C1=C(C=CC(=C1)C(=O)C1=CC(=C(C=C1)C)C1(CCCCC1)C)C TXNJMRAUGLOGEY-UHFFFAOYSA-N 0.000 description 1
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OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
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Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/12—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Diabetes (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Hematology (AREA)
Endocrinology (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Obesity (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Emergency Medicine (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Medicinal Preparation (AREA)

NL8800805A 1987-04-01 1988-03-30 Gesubstitueerde 1,3-dioxolaan en 1,3-dioxaanderivaten, werkwijzen voor de bereiding van deze derivaten en hun toepassing. NL8800805A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US3411887A	1987-04-01	1987-04-01
US3411887		1987-04-01

Publications (1)

Publication Number	Publication Date
NL8800805A true NL8800805A (nl)	1988-11-01

Family

ID=21874422

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8800805A NL8800805A (nl)	1987-04-01	1988-03-30	Gesubstitueerde 1,3-dioxolaan en 1,3-dioxaanderivaten, werkwijzen voor de bereiding van deze derivaten en hun toepassing.

Country Status (18)

Country	Link
JP (1)	JPS63277672A (fr)
KR (1)	KR880012224A (fr)
AU (1)	AU1400788A (fr)
BE (1)	BE1000783A3 (fr)
DE (1)	DE3810874A1 (fr)
DK (1)	DK179288A (fr)
ES (1)	ES2011831A6 (fr)
FR (1)	FR2613226B1 (fr)
GB (1)	GB2202849A (fr)
GR (1)	GR880100196A (fr)
HU (1)	HUT50156A (fr)
IL (1)	IL85920A0 (fr)
IT (1)	IT1219895B (fr)
LU (1)	LU87176A1 (fr)
NL (1)	NL8800805A (fr)
PT (1)	PT87127B (fr)
SE (1)	SE8801166L (fr)
ZA (1)	ZA882350B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8701961D0 (en) *	1987-01-29	1987-03-04	Unilever Plc	Perfumery materials

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3235589A1 (de) *	1982-09-25	1984-03-29	Hoechst Ag, 6230 Frankfurt	Benzylether von phenol-mannich-basen, verfahren zu ihrer herstellung, ihre verwendung sowie pharmazeutische praeparate auf basis dieser verbindungen, zwischenprodukte und verfahren zu deren herstellung

1988
- 1988-03-23 LU LU87176A patent/LU87176A1/fr unknown
- 1988-03-28 BE BE8800360A patent/BE1000783A3/fr not_active IP Right Cessation
- 1988-03-28 FR FR888804153A patent/FR2613226B1/fr not_active Expired
- 1988-03-29 GB GB08807503A patent/GB2202849A/en not_active Withdrawn
- 1988-03-29 GR GR880100196A patent/GR880100196A/el unknown
- 1988-03-29 SE SE8801166A patent/SE8801166L/xx not_active Application Discontinuation
- 1988-03-30 IT IT47797/88A patent/IT1219895B/it active
- 1988-03-30 AU AU14007/88A patent/AU1400788A/en not_active Abandoned
- 1988-03-30 NL NL8800805A patent/NL8800805A/nl not_active Application Discontinuation
- 1988-03-30 ES ES8801002A patent/ES2011831A6/es not_active Expired - Lifetime
- 1988-03-30 HU HU881581A patent/HUT50156A/hu unknown
- 1988-03-30 KR KR1019880003491A patent/KR880012224A/ko not_active Withdrawn
- 1988-03-30 DE DE3810874A patent/DE3810874A1/de not_active Withdrawn
- 1988-03-30 IL IL85920A patent/IL85920A0/xx unknown
- 1988-03-30 PT PT87127A patent/PT87127B/pt not_active IP Right Cessation
- 1988-03-30 DK DK179288A patent/DK179288A/da not_active Application Discontinuation
- 1988-03-31 ZA ZA882350A patent/ZA882350B/xx unknown
- 1988-03-31 JP JP63081182A patent/JPS63277672A/ja active Pending

Also Published As

Publication number	Publication date
ZA882350B (en)	1989-12-27
BE1000783A3 (fr)	1989-04-04
GB2202849A (en)	1988-10-05
FR2613226B1 (fr)	1989-09-15
DE3810874A1 (de)	1988-10-20
DK179288D0 (da)	1988-03-30
GB8807503D0 (en)	1988-05-05
ES2011831A6 (es)	1990-02-16
IT8847797A0 (it)	1988-03-30
KR880012224A (ko)	1988-11-26
SE8801166D0 (sv)	1988-03-29
GR880100196A (el)	1989-01-31
DK179288A (da)	1988-10-02
IL85920A0 (en)	1988-09-30
PT87127A (pt)	1988-04-01
PT87127B (pt)	1992-07-31
HUT50156A (en)	1989-12-28
AU1400788A (en)	1988-10-06
LU87176A1 (fr)	1988-11-17
SE8801166L (sv)	1988-10-02
FR2613226A1 (fr)	1988-10-07
IT1219895B (it)	1990-05-24
JPS63277672A (ja)	1988-11-15

Legal Events

Date	Code	Title	Description
1991-11-01	BV	The patent application has lapsed

Publication	Publication Date	Title
EP0017195B1 (fr)	1984-07-04	Dérivés de cyclohexane-1,3-diones substitués en positions 2 et 5, procédé pour leur préparation et composition pharmaceutique les contenant
US3174901A (en)	1965-03-23	Process for the oral treatment of diabetes
JPH07502487A (ja)	1995-03-16	血糖低下性チアゾリジンジオンとその中間体
NL8800805A (nl)	1988-11-01	Gesubstitueerde 1,3-dioxolaan en 1,3-dioxaanderivaten, werkwijzen voor de bereiding van deze derivaten en hun toepassing.
US3923994A (en)	1975-12-02	Anti-arthritic compositions comprising a 3-aryl 2-thiohydantoin and methods of producing anti-arthritic acitvity
FR2640271A1 (fr)	1990-06-15	Nouveaux derives de l'adenosine, leur preparation et leur utilisation comme medicaments
NL8101987A (nl)	1981-11-16	De verbinding 4-amino-1-beta-d-ribofuranosyl-1h-imidazo/4.5-c/-pyridine of een farmaceutisch aanvaardbaar zuuradditiezout daarvan; farmaceutisch preparaat.
JPS61275275A (ja)	1986-12-05	１，３−ジチオ−ル−２−イリデン誘導体
US3953601A (en)	1976-04-27	Dibenzothiophene derivatives as serum lipid lowering agents
EP0534655B1 (fr)	1995-06-28	Thiazolidine-2,4-diones pour le traitement de l'hypertension
US4320135A (en)	1982-03-16	Inhibiting growth hormone secretion with 5,5-substituted hydantoin derivatives
US4801589A (en)	1989-01-31	Method for suppressing the immune response
US3968247A (en)	1976-07-06	Substituted or unsubstituted p-alkanoyl toluenes as anti-diabetic agents
KR950003499B1 (ko)	1995-04-13	1,3,5-트리티안 유도체
US3941888A (en)	1976-03-02	Substituted or unsubstituted p-alkanoyl toluenes as hypolipidemics
FR2605006A1 (fr)	1988-04-15	Derives du 5-fluorouracile, procede pour leur preparation, composition anticancereuse les contenant et leur utilisation pour la preparation d'une composition destinee au traitement d'un cancer
US3222365A (en)	1965-12-07	4-halophenyl-2-alkyl-1(2)-phthalazinones
US3562256A (en)	1971-02-09	1,3-dialkyl-5-(substituted arylsulfonyl)-tetrahydro-1,3,5-triazine-4-thiones
US4057630A (en)	1977-11-08	Antiarthritic compositions comprising bis-coordinated gold(1+) salts and methods of producing antiarthritic activity
JPS6029693B2 (ja)	1985-07-12	１−オキソ−２，２−ジ置換−５−インダニロキシアルカノイツクアシツドの製法
EP0455830A1 (fr)	1991-11-13	Medicament contenant un derive de dioxyde de thiazine
JPH0256424A (ja)	1990-02-26	肝疾患治療剤
US3821378A (en)	1974-06-28	2-amino-4,6-diphenethylamino-s-triazine as active serum cholesterol lowering agent
US4093719A (en)	1978-06-06	Antiarthritic compositions comprising bis[(trialkyl-phosphine)gold(I)]sulfides and methods of producing antiarthritic activity
JPS59164330A (ja)	1984-09-17	ポリシルセスキオキサン