DE1816097A1 - Salze der Orotsaeure - Google Patents

Salze der Orotsaeure

Info

Publication number: DE1816097A1
Authority: DE; Germany
Prior art keywords: acid; amine; orotic; amines; orotate
Prior art date: 1967-12-21
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.): Pending

Application number

DE19681816097

Other languages

German (de)

English (en)

Inventor

Emil Hofstetter

Dr Rolf Pfirrmann

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.)

Ed Geistlich Soehne AG fuer Chemische Industrie

Original Assignee

Ed Geistlich Soehne AG fuer Chemische Industrie

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.)

1967-12-21

Filing date

1968-12-20

Publication date

1969-09-25

1968-12-20 Application filed by Ed Geistlich Soehne AG fuer Chemische Industrie filed Critical Ed Geistlich Soehne AG fuer Chemische Industrie

1969-09-25 Publication of DE1816097A1 publication Critical patent/DE1816097A1/de

Status Pending legal-status Critical Current

Links

-1 Amine salts Chemical class 0.000 title claims abstract description 11
239000002253 acid Substances 0.000 title claims abstract description 8
150000007513 acids Chemical class 0.000 title description 2
PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical class OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 claims abstract description 59
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 28
UFIVEPVSAGBUSI-UHFFFAOYSA-N dihydroorotic acid Chemical class OC(=O)C1CC(=O)NC(=O)N1 UFIVEPVSAGBUSI-UHFFFAOYSA-N 0.000 claims abstract description 21
150000003839 salts Chemical class 0.000 claims abstract description 21
150000001412 amines Chemical class 0.000 claims abstract description 13
239000002904 solvent Substances 0.000 claims abstract description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
229960005010 orotic acid Drugs 0.000 claims description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 9
238000000034 method Methods 0.000 claims description 9
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
239000004480 active ingredient Substances 0.000 claims description 6
229960002887 deanol Drugs 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
150000005619 secondary aliphatic amines Chemical class 0.000 claims description 4
150000003510 tertiary aliphatic amines Chemical class 0.000 claims description 4
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
XGIKILRODBEJIL-UHFFFAOYSA-N 1-(ethylamino)ethanol Chemical compound CCNC(C)O XGIKILRODBEJIL-UHFFFAOYSA-N 0.000 claims description 2
HZLYGAQNCRJBDT-UHFFFAOYSA-N 2-(ethylamino)propan-2-ol Chemical compound CCNC(C)(C)O HZLYGAQNCRJBDT-UHFFFAOYSA-N 0.000 claims description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
229940072049 amyl acetate Drugs 0.000 claims description 2
PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims description 2
150000004292 cyclic ethers Chemical class 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
125000003595 primary aliphatic amine group Chemical group 0.000 claims description 2
150000003139 primary aliphatic amines Chemical class 0.000 claims description 2
YEISHPLKFCURHG-UHFFFAOYSA-N CN(C)C(C(N1)=O)=C(C(O)=O)NC1=O Chemical compound CN(C)C(C(N1)=O)=C(C(O)=O)NC1=O YEISHPLKFCURHG-UHFFFAOYSA-N 0.000 claims 1
ROHGCLWGNSVXHD-UHFFFAOYSA-N 2-(dimethylamino)ethanol;2,4-dioxo-1h-pyrimidine-6-carboxylic acid Chemical compound CN(C)CCO.OC(=O)C1=CC(=O)NC(=O)N1 ROHGCLWGNSVXHD-UHFFFAOYSA-N 0.000 abstract description 7
125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
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239000002775 capsule Substances 0.000 description 5
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 4
OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 4
239000007938 effervescent tablet Substances 0.000 description 4
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 4
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239000011782 vitamin Substances 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
230000017531 blood circulation Effects 0.000 description 3
238000001816 cooling Methods 0.000 description 3
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235000010374 vitamin B1 Nutrition 0.000 description 3
239000011691 vitamin B1 Substances 0.000 description 3
235000019163 vitamin B12 Nutrition 0.000 description 3
239000011715 vitamin B12 Substances 0.000 description 3
235000019164 vitamin B2 Nutrition 0.000 description 3
239000011716 vitamin B2 Substances 0.000 description 3
235000019154 vitamin C Nutrition 0.000 description 3
239000011718 vitamin C Substances 0.000 description 3
FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 2
239000002126 C01EB10 - Adenosine Substances 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 description 2
ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 2
IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical compound OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O IMQLKJBTEOYOSI-GPIVLXJGSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
IMQLKJBTEOYOSI-UHFFFAOYSA-N Phytic acid Natural products OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 description 2
AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 2
FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 2
229930003451 Vitamin B1 Natural products 0.000 description 2
229930003779 Vitamin B12 Natural products 0.000 description 2
229930003471 Vitamin B2 Natural products 0.000 description 2
229930003268 Vitamin C Natural products 0.000 description 2
QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 description 2
229960005305 adenosine Drugs 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
ZFXVRMSLJDYJCH-UHFFFAOYSA-N calcium magnesium Chemical compound [Mg].[Ca] ZFXVRMSLJDYJCH-UHFFFAOYSA-N 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
QWJSAWXRUVVRLH-UHFFFAOYSA-M choline bitartrate Chemical compound C[N+](C)(C)CCO.OC(=O)C(O)C(O)C([O-])=O QWJSAWXRUVVRLH-UHFFFAOYSA-M 0.000 description 2
229960004874 choline bitartrate Drugs 0.000 description 2
AGVAZMGAQJOSFJ-WZHZPDAFSA-M cobalt(2+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+2].N#[C-].[N-]([C@@H]1[C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@@H](C)OP(O)(=O)O[C@H]3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)\C2=C(C)/C([C@H](C\2(C)C)CCC(N)=O)=N/C/2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O AGVAZMGAQJOSFJ-WZHZPDAFSA-M 0.000 description 2
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
230000000694 effects Effects 0.000 description 2
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231100000053 low toxicity Toxicity 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
229940091250 magnesium supplement Drugs 0.000 description 2
SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 2
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239000002184 metal Substances 0.000 description 2
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229940087332 rutin 10 mg Drugs 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000829 suppository Substances 0.000 description 2
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DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 2
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DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 1
SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 description 1
PMVSDNDAUGGCCE-TYYBGVCCSA-L Ferrous fumarate Chemical compound [Fe+2].[O-]C(=O)\C=C\C([O-])=O PMVSDNDAUGGCCE-TYYBGVCCSA-L 0.000 description 1
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QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
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230000029058 respiratory gaseous exchange Effects 0.000 description 1
230000000552 rheumatic effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000014616 translation Effects 0.000 description 1
235000019158 vitamin B6 Nutrition 0.000 description 1
239000011726 vitamin B6 Substances 0.000 description 1
150000003710 vitamin D derivatives Chemical class 0.000 description 1
QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
235000005282 vitamin D3 Nutrition 0.000 description 1
239000011647 vitamin D3 Substances 0.000 description 1
235000019165 vitamin E Nutrition 0.000 description 1
239000011709 vitamin E Substances 0.000 description 1
235000019168 vitamin K Nutrition 0.000 description 1
239000011712 vitamin K Substances 0.000 description 1
229940089133 vitamin b6 5 mg Drugs 0.000 description 1
229940046008 vitamin d Drugs 0.000 description 1
229940021056 vitamin d3 Drugs 0.000 description 1
150000003722 vitamin derivatives Chemical class 0.000 description 1
230000036642 wellbeing Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/557—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. orotic acid

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DE19681816097 1967-12-21 1968-12-20 Salze der Orotsaeure Pending DE1816097A1 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB5814067A GB1182320A (en)	1967-12-21	1967-12-21	Dihydroorotic and Salts

Publications (1)

Publication Number	Publication Date
DE1816097A1 true DE1816097A1 (de)	1969-09-25

Family

ID=10480857

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19681816097 Pending DE1816097A1 (de)	1967-12-21	1968-12-20	Salze der Orotsaeure

Country Status (7)

Country	Link
BE (1)	BE725874A (xx)
CH (1)	CH510674A (xx)
DE (1)	DE1816097A1 (xx)
ES (1)	ES361702A1 (xx)
FR (1)	FR8234M (xx)
GB (1)	GB1182320A (xx)
NL (1)	NL6818217A (xx)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2005002554A3 (en) *	2003-06-13	2005-06-16	Procter & Gamble	A method of promoting sleep using topical administration of vasoactive agents

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3912477A1 (de) *	1989-04-15	1990-10-18	Mueller Robert Dr	Aeusserlich anzuwendendes praeparat und seine verwendung
US7396526B1 (en)	1998-11-12	2008-07-08	Johnson & Johnson Consumer Companies, Inc.	Skin care composition
US6607735B2 (en)	2000-12-21	2003-08-19	Johnson & Johnson Consumer Companies, Inc.	Method for reducing the appearance of dark circles under the eyes

1967
- 1967-12-21 GB GB5814067A patent/GB1182320A/en not_active Expired
1968
- 1968-12-18 NL NL6818217A patent/NL6818217A/xx unknown
- 1968-12-19 CH CH1891168A patent/CH510674A/de not_active IP Right Cessation
- 1968-12-19 FR FR179091A patent/FR8234M/fr not_active Expired
- 1968-12-20 ES ES361702A patent/ES361702A1/es not_active Expired
- 1968-12-20 BE BE725874D patent/BE725874A/xx unknown
- 1968-12-20 DE DE19681816097 patent/DE1816097A1/de active Pending

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2005002554A3 (en) *	2003-06-13	2005-06-16	Procter & Gamble	A method of promoting sleep using topical administration of vasoactive agents

Also Published As

Publication number	Publication date
FR8234M (xx)	1970-09-28
CH510674A (de)	1971-07-31
GB1182320A (en)	1970-02-25
NL6818217A (xx)	1969-06-24
ES361702A1 (es)	1970-11-16
BE725874A (xx)	1969-06-20

Publication	Publication Date	Title
EP0044801B1 (de)	1984-02-15	Nichthygroskopische Salze der 4-Hydroxybuttersäure, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung pharmazeutischer Mittel
DE69325451T2 (de)	2000-01-20	Verwendung von pyruvamid und ausgewählten pyruvyl-aminosäuren
DE2607620C2 (de)	1984-09-13	4-Amino-5-hexensäure und Verfahren zu deren Herstellung
DE2446010A1 (de)	1975-04-03	4-(monoalkylamino)benzoesaeurederivate und verfahren zu ihrer herstellung
DE2165962C2 (de)	1982-05-13	4-Hydroxy-6-arylpyrimidine
EP0402755A2 (de)	1990-12-19	L-Carnitin-Magnesium-Zitrat
CH630881A5 (de)	1982-07-15	Verfahren zur herstellung neuer substituierter fluoracylresorcine.
EP0009633B1 (de)	1982-09-22	3,4,5-Trihydroxypiperidin-Derivate, Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel und Tierfuttermittel
EP0034784A1 (de)	1981-09-02	Derivate des 3,4,5-Trihydroxypiperidins, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel sowie in der Tierernährung
CH644263A5 (de)	1984-07-31	Fuer kosmetische zwecke verwendbare praeparate und verfahren zur herstellung der wirkstoffe dieser praeparate.
DE2118109A1 (de)	1971-12-02	Neue chemische Verbindung
DE1816097A1 (de)	1969-09-25	Salze der Orotsaeure
DE2721987C2 (de)	1985-08-14	p-Acetamidophenyldiäthylaminoacetat, dessen pharmakologisch unbedenkliche Additionssalze, Verfahren zu deren Herstellung und Arzneimittel mit diesen Verbindungen als Wirkstoff
CH621333A5 (xx)	1981-01-30
DE3688807T2 (de)	1994-02-10	Isolierung von Castanospermin und dessen Verwendung als antidiabetisches Heilmittel.
DE2708826A1 (de)	1977-09-08	Substituierte 8-azapurine und verfahren zu ihrer herstellung
DE3425466A1 (de)	1985-01-24	Synergistisches arzneimittelpraeparat zur behandlung von leberkrankheiten
DE2411823A1 (de)	1974-09-26	Verwendung von 1,2,4-triazol-3-carboxamiden und -thiocarboxamiden als antivirenmittel
DE2703652C2 (xx)	1988-01-21
DE2522218C3 (de)	1981-04-02	Zusammensetzung für die Human- oder Veterinärmedizin, Methylaminderivate und Verfahren zu deren Herstellung
DE2407016C3 (de)	1980-06-19	2-Alkoxybenzoylaminocarbonsäuren, Verfahren zu deren Herstellung und diese Verbindungen enthaltende antipyretische Mittel
DE1911240C3 (de)	1979-06-13	Antibioticum 20 798 RP, Verfahren zu seiner Gewinnung und Arzneimittel, die dieses enthalten
DE951723C (de)	1956-10-31	Verfahren zur Herstellung N-substituierter Normorphin- oder Dihydronormorphinverbindungen bzw. deren Estern und Salzen
DE2723450A1 (de)	1977-12-15	Uracilderivate und verfahren zu ihrer herstellung
DE2625110A1 (de)	1977-01-13	Cyclopropanolderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel

Legal Events

Date	Code	Title	Description
1971-04-22	SH	Request for examination between 03.10.1968 and 22.04.1971

DE1816097A1 - Salze der Orotsaeure - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (1)

Publications (1)

Family

ID=10480857

Family Applications (1)

Country Status (7)

Cited By (1)

Families Citing this family (3)

Cited By (1)

Also Published As

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